References
- Moiseev, D. V.; James, B. R. Tetrakis(Hydroxymethyl) Phosphonium Salts: Their Properties, Hazards and Toxicities. Phosphorus Sulfur Silicon Relat. Elem. 2020, 195, 263–279. DOI: https://doi.org/10.1080/10426507.2019.1686379.
- Moiseev, D. V.; James, B. R. Syntheses and Rearrangements of Tris(Hydroxymethyl)Phosphine and Tetrakis(Hydroxymethyl) Phosphonium Salts. Phosphorus Sulfur Silicon Relat. Elem. 2020, 195, 687–712. DOI: https://doi.org/10.1080/10426507.2020.1764957.
- Hoffman, A. The Action of Hydrogen Phosphide on Formaldehyde. J. Am. Chem. Soc. 1921, 43, 1684–1688. DOI: https://doi.org/10.1021/ja01440a035.
- Reeves, W. A.; Guthrie, J. D. Flameproof Fibrous Aminoethylated Cellulose Derivatives. U.S. Patent 2,668,096, Feb 2, 1954.
- Evans, J. G.; Landells, G.; Perfect, J. R. W.; Topley, B.; Coates, H. Polymeric Materials. Br. Patent 761,985, Nov 21, 1956.
- Reeves, W. A.; Guthrie, J. D. Intermediate for Flame-Resistant Polymers - Reactions of Tetrakis(Hydroxymethyl)Phosphonium Chloride. Ind. Eng. Chem. 1956, 48, 64–67. DOI: https://doi.org/10.1021/ie50553a021.
- Boyer, N. E.; Vajda, A. E. Fireproofing of Polymers with Derivatives of Phosphines and with Halogen-Phosphorus Compounds. Polym. Eng. Sci. 1964, 4, 45–55. DOI: https://doi.org/10.1002/pen.760040111.
- Horrocks, A. R. Flame Retardant Challenges for Textiles and Fibres: New Chemistry versus Innovatory Solutions. Polym. Degrad. Stab. 2011, 96, 377–392. DOI: https://doi.org/10.1016/j.polymdegradstab.2010.03.036.
- Reeves, W. A.; Guthrie, J. D. Phosphorus-Containing Polypeptides U.S. Patent 2,768,997, Oct 30, 1956.
- Jirasek, A.; Hilts, M.; Shaw, C.; Baxter, P. Experimental Properties of THPC Based Normoxic Polyacrylamide Gels for Use in X-Ray Computed Tomography Gel Dosimetry. J. Phys.: Conf. Ser. 2006, 56, 263–267. DOI: https://doi.org/10.1088/1742-6596/56/1/045.
- Lim, D. W.; Nettles, D. L.; Setton, L. A.; Chilkoti, A. Rapid Cross-Linking of Elastin-like Polypeptides with (Hydroxymethyl) Phosphines in Aqueous Solution. Biomacromolecules 2007, 8, 1463–1470. DOI: https://doi.org/10.1021/bm061059m.
- Ahn, W.; Lee, J.-H.; Kim, S. R.; Lee, J.; Lee, E. J. Designed Protein- and Peptide-Based Hydrogels for Biomedical Sciences. J. Mater. Chem. B. 2021, 9, 1919–1940. DOI: https://doi.org/10.1039/D0TB02604B.
- Grekov, L. I.; Vladimtseva, I. V.; Efremenko, V. I.; Trofimov, E. N.; Stolbin, S. V. Method of Sorbent Production. U.S.S.R Patent 1,643,073, Apr 23, 1991.
- Henderson, W.; Petach, H. H.; Sarfo, K. A Novel Polymeric Phosphine Oxide-Derived Support for Enzyme Immobilization. J. Chem. Soc. Chem. Commun. 1994, 245–246. DOI: https://doi.org/10.1039/c39940000245.
- Petach, H. H.; Henderson, W.; Olsen, G. M. P(CH2OH)3—A New Coupling Reagent for the Covalent Immobilisation of Enzymes. J. Chem. Soc. Chem. Commun. 1994, 2181–2182. DOI: https://doi.org/10.1039/c39940002181.
- Bonnington, L. S.; Henderson, W.; Petach, H. H. P(CH2OH)3-Polyetheramine-Derived Polymeric Films for Enzyme Immobilization. Enzyme Microb. Technol. 1995, 17, 746–750. DOI: https://doi.org/10.1016/0141-0229(95)00001-L.
- Ekubo, A. T. The Chemistry of New Cyclic Phosphorus(III) Ligands. Ph.D. Dissertation, Loughborough University, Loughborough, UK, 2009.
- Lastra-Calvo, N. Synthesis of Novel Aminomethylphosphine Complexes. Ph.D. Dissertation, Loughborough University, Loughborough, UK, 2014.
- Phillips, A. D.; Gonsalvi, L.; Romerosa, A.; Vizza, F.; Peruzzini, M. Coordination Chemistry of 1,3,5-Triaza-7-Phosphaadamantane (PTA). Transition Metal Complexes and Related Catalytic, Medicinal and Photoluminescent Applications. Coord. Chem. Rev. 2004, 248, 955–993. DOI: https://doi.org/10.1016/j.ccr.2004.03.010.
- Müller, T. J. J. Relative Reactivities of Functional Groups as the Key to Multicomponent Reactions. In Science of Synthesis: Multicomponent Reactions; Müller, T. J. J., Ed.; Thieme, 2014; Vol. 1, pp 5–27. DOI: https://doi.org/10.1055/sos-SD-210-00002.
- Tramontini, M. Advances in the Chemistry of Mannich Bases. Synthesis 1973, 1973, 703–775. DOI: https://doi.org/10.1055/s-1973-22294.
- Kleinman, E. F. The Bimolecular Aliphatic Mannich and Related Reactions. In Comprehensive Organic Synthesis, 1st ed.; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, pp 893–951. DOI: https://doi.org/10.1016/B978-0-08-052349-1.00052-4.
- Heaney, H. The Bimolecular Aromatic Mannich Reaction. In Comprehensive Organic Synthesis, 1st ed.; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, pp 953–973. DOI: https://doi.org/10.1016/B978-0-08-052349-1.00053-6.
- Arend, M.; Westermann, B.; Risch, N. Modern Variants of the Mannich Reaction. Angew. Chem. Int. Ed. 1998, 37, 1044–1070. DOI: https://doi.org/10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO;2-E.
- Verkade, J. M. M.; van Hemert, L. J. C.; Quaedflieg, P. J. L. M.; Rutjes, F. P. J. T. Organocatalysed Asymmetric Mannich Reactions. Chem. Soc. Rev. 2008, 37, 29–41. DOI: https://doi.org/10.1039/B713885G.
- Benohoud, M.; Hayashi, Y. Mannich Reaction and Baylis–Hillman Reaction. In Science of Synthesis: Water in Organic Synthesis; Kobayashi, S., Ed.; Thieme, 2012, pp 385–432. DOI: https://doi.org/10.1055/sos-SD-206-00288.
- Bernardi, L.; Ricci, A. Third Component Enolizable Carbonyl Compound (Mannich Reaction). In Science of Synthesis: Multicomponent Reactions; Müller, T. J. J., Ed.; Thieme, 2014; Vol. 1, pp 123–164. DOI: https://doi.org/10.1055/sos-SD-210-00078.
- Salim, S.; Harry, N. A.; Krishnan, K. K.; Anilkumar, G. Recent Developments and Perspectives in Asymmetric Mannich Reaction. Asian J. Org. Chem. 2018, 7, 613–633. DOI: https://doi.org/10.1002/ajoc.201700679.
- Roman, G. Mannich Bases in Medicinal Chemistry and Drug Design. Eur. J. Med. Chem. 2015, 89, 743–816. DOI: https://doi.org/10.1016/j.ejmech.2014.10.076.
- Thompson, B. B. The Mannich Reaction. Mechanistic and Technological Considerations. J. Pharm. Sci. 1968, 57, 715–733. DOI: https://doi.org/10.1002/jps.2600570501.
- Noble, A.; Anderson, J. C. Nitro-Mannich Reaction. Chem. Rev. 2013, 113, 2887–2939. DOI: https://doi.org/10.1021/cr300272t.
- Enders, D.; Shilvock, J. P. Some Recent Applications of α-Amino Nitrile Chemistry. Chem. Soc. Rev. 2000, 29, 359–373. DOI: https://doi.org/10.1039/a908290e.
- Ayaz, M.; Moliner, F. D.; Morales, G. A.; Hulme, C. Third Component Cyanide (Strecker and Strecker-Type Reactions). In Science of Synthesis: Multicomponent Reactions; Müller, T. J. J., Ed.; Thieme, 2014; Vol. 1, pp 99–122. DOI: https://doi.org/10.1055/sos-SD-210-00029.
- Declerck, V.; Martinez, J.; Lamaty, F. Aza-Baylis-Hillman Reaction. Chem. Rev. 2009, 109, 1–48. DOI: https://doi.org/10.1021/cr068057c.
- Peshkov, V. A.; Pereshivko, O. P.; Eycken, E. V. A. A Walk Around the A3-Coupling. Chem. Soc. Rev. 2012, 41, 3790–3807. DOI: https://doi.org/10.1039/C2CS15356D.
- Lauder, K.; Toscani, A.; Scalacci, N.; Castagnolo, D. Synthesis and Reactivity of Propargylamines in Organic Chemistry. Chem. Rev. 2017, 117, 14091–14200. DOI: https://doi.org/10.1021/acs.chemrev.7b00343.
- Rokade, B. V.; Barker, J.; Guiry, P. J. Development of and Recent Advances in Asymmetric A3 Coupling. Chem. Soc. Rev. 2019, 48, 4766–4790. DOI: https://doi.org/10.1039/C9CS00253G.
- Weiner, B.; Szymański, W.; Janssen, D. B.; Minnaard, A. J.; Feringa, B. L. Recent Advances in the Catalytic Asymmetric Synthesis of β-Amino Acids. Chem. Soc. Rev. 2010, 39, 1656–1691. DOI: https://doi.org/10.1039/B919599H.
- Vesely, J.; Rios, R. Enantioselective Methodologies Using N-Carbamoyl-Imines. Chem. Soc. Rev. 2014, 43, 611–630. DOI: https://doi.org/10.1039/C3CS60321K.
- Eftekhari-Sis, B.; Zirak, M. α-Imino Esters in Organic Synthesis: Recent Advances. Chem. Rev. 2017, 117, 8326–8419. DOI: https://doi.org/10.1021/acs.chemrev.7b00064.
- Hellmann, H.; Opitz, G. Aminomethylierung. Eine Studie zur Aufklärung und Einordnung der Mannich-Reaction. Angew. Chem. 1956, 68, 265–272. DOI: https://doi.org/10.1002/ange.19560680803.
- Tramontini, M.; Angiolini, L. Mannich Bases. Chemistry and Uses. Rees, C. W., Ed.; CRC Press: Boca Raton, 1994.
- Kostyanovskii, R. G.; Él'natanov, Y. I.; Shikhaliev, S. M.; Ignatov, S. M.; Chervin, I. I. Geminal Systems. 19. Reactions of Aminomethylphosphines with Electrophilic Reagents. Russ. Chem. Bull. 1982, 31, 1433–1441. DOI: https://doi.org/10.1007/BF00954168.
- Petrov, K. A.; Chauzov, V. A.; Erokhina, T. S. Aminoalkyl Organophosphorus Compounds. Russ. Chem. Rev. 1974, 43, 984–1006. DOI: https://doi.org/10.1070/RC1974v043n11ABEH001877.
- Cherkasov, R. A.; Galkin, V. I. The Kabachnik–Fields Reaction: Synthetic Potential and the Problem of the Mechanism. Russ. Chem. Rev. 1998, 67, 857–882. DOI: https://doi.org/10.1070/RC1998v067n10ABEH000421.
- Keglevich, G.; Bálint, E. The Kabachnik-Fields Reaction: Mechanism and Synthetic Use. Molecules 2012, 17, 12821–12835. DOI: https://doi.org/10.3390/molecules171112821.
- Ali, T. E.; Abdel-Kariem, S. M. Methods for the Synthesis of α-Heterocyclic/Heteroaryl-α-Aminophosphonic Acids and Their Esters. ARKIVOC 2015, VI, 246–287. DOI: https://doi.org/10.3998/ark.5550190.p009.112.
- Zefirov, N. S.; Matveeva, E. D.; Shuvalov, M. V. Third Component Phosphonate (Kabachnik–Fields Reaction). In Science of Synthesis: Multicomponent Reactions; Müller, T. J. J., Ed.; Thieme, 2014; Vol. 1, pp 273–295. DOI: https://doi.org/10.1055/sos-SD-210-00157.
- Moedritzer, K.; Irani, R. R. The Direct Synthesis of α-Aminomethylphosphonic Acids. Mannich-Type Reactions with Orthophosphorous Acid. J. Org. Chem. 1966, 31, 1603–1607. DOI: https://doi.org/10.1021/jo01343a067.
- Sevrain, C. M.; Berchel, M.; Couthon, H.; Jaffrès, P.-A. Phosphonic Acid: Preparation and Applications. Beilstein J. Org. Chem. 2017, 13, 2186–2213. DOI: https://doi.org/10.3762/bjoc.13.219.
- Merino, P.; Marques-Lopez, E.; Herrera, R. P. Catalytic Enantioselective Hydrophosphonylation of Aldehydes and Imines. Adv. Synth. Catal. 2008, 350, 1195–1208. DOI: https://doi.org/10.1002/adsc.200800131.
- Birum, G. H. Urylenediphosphonates. General Method for the Synthesis of α-Ureidophosphonates and Related Structures. J. Org. Chem. 1974, 39, 209–213. DOI: https://doi.org/10.1021/jo00916a019.
- Oleksyszyn, J.; Subotkowska, L.; Mastalerz, P. Diphenyl 1-Aminoalkanephosphonates. Synthesis 1979, 985–986. DOI: https://doi.org/10.1055/s-1979-28903.
- Oleksyszyn, J.; Gruszecka, E. Amidoalkylation of Phosphorous Acid. Tetrahedron Lett. 1981, 22, 3537–3540. DOI: https://doi.org/10.1016/S0040-4039(01)81951-1.
- Kudzin, M. H.; Kudzin, Z. H.; Drabowicz, J. Thioureidoalkylphosphonates in the Synthesis of 1-Aminoalkylphosphonic Acids: The Ptc-Aminophosphonate Method. ARKIVOC 2011, VI, 227–269. DOI: https://doi.org/10.3998/ark.5550190.0012.617.
- Daigle, D. J.; Frank, A. W. Chemistry of Hydroxymethyl Phosphorus Compounds: Part IV. Ammonia, Amines, and THPOH: A Chemical Approach to Flame Retardancy. Text. Res. J. 1982, 52, 751–755. DOI: https://doi.org/10.1177/004051758205201203.
- Kellner, K.; Tzschach, A. Die Mannich-Reaktion als Synthesekonzept in der Phosphinchemie. Z. Chem. 1984, 24, 365–375. DOI: https://doi.org/10.1002/zfch.19840241004.
- Erastov, O. A.; Nikonov, G. N. Tertiary Phosphines with Functional-Group Substituents. Russ. Chem. Rev. 1984, 53, 369–382. DOI: https://doi.org/10.1070/RC1984v053n04ABEH003057.
- Arbuzov, B. A.; Nikonov, G. N. Phosphorus Heterocycles from α-Hydroxyalkylphosphines and Vinylphosphines. Adv. Heterocycl. Chem. 1994, 61, 59–140. DOI: https://doi.org/10.1016/S0065-2725(08)60897-1.
- Karasik, A. A.; Balueva, A. S.; Sinyashin, O. G. An Effective Strategy of P,N-Containing Macrocycle Design. C. R. Chimie. 2010, 13, 1151–1167. DOI: https://doi.org/10.1016/j.crci.2010.04.006.
- Musina, E. I.; Karasik, A. A.; Sinyashin, O. G.; Nikonov, G. N. Heterocyclic Phosphines with P-C-X Fragments (X = O, N, P). Adv. Heterocycl. Chem. 2015, 117, 83–130. DOI: https://doi.org/10.1016/bs.aihch.2015.10.001.
- Karasik, A. A.; Balueva, A. S.; Musina, E. I.; Sinyashin, O. G. Chelating Cyclic Aminomethylphosphines and Their Transition Metal Complexes as a Promising Basis of Bioinspired Mimetic Catalysts. Mendeleev Commun. 2013, 23, 237–248. DOI: https://doi.org/10.1016/j.mencom.2013.09.001.
- Heaney, F. Functions Containing a Nitrogen and Another Group 15 Element. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon, 1995; Vol. 4, pp 451–504. DOI: https://doi.org/10.1016/B0-08-044705-8/00255-7.
- Issleib, K. Element-Phosphor-Heterocyclen. Phosphorus Sulfur Silicon Relat. Elem. 1976, 2, 219–235. DOI: https://doi.org/10.1080/03086647608078954.
- Karasik, A. A.; Musina, E. I.; Balueva, A. S.; Strelnik, I. D.; Sinyashin, O. G. Cyclic Aminomethylphosphines as Ligands. Rational Design and Unpredicted Findings. Pure Appl. Chem. 2017, 89, 293–310. DOI: https://doi.org/10.1515/pac-2016-1022.
- Frank, A. W.; Daigle, D. J.; Vail, S. L. Chemistry of Hydroxymethyl Phosphorus Compounds: Part II. Phosphonium Salts. Text. Res. J. 1982, 52, 678–693. DOI: https://doi.org/10.1177/004051758205201102.
- Baimukhametov, F. Z. Synthesis and Properties of New Primary Phosphines and Aminomethylphosphines with Functionalized Substituents at the Phosphorus Atom. Ph.D. Dissertation, A. E. Arbuzov Institute of Organic and Physical Chemistry, Russian Federation, Kazan, 2002.
- Naumov, R. N. Synthesis of New Heterocyclic Di- and Tetraphosphines and Their Complexes with Transition Metals of VII, VIII Groups. Ph.D. Dissertation, A. E. Arbuzov Institute of Organic and Physical Chemistry, Russian Federation, Kazan, 2006.
- Serindag, O. The Synthesis of Some Aminobis(Methylphosphines) and Their Transition Metal Complexes. Ph.D. Dissertation, University of Leicester, Leicester, UK, 1993.
- Wittmann, T. I. New 14-Membered Cyclic Tetrakisphosphines and Their Complexes with Transition Metals: Synthesis and Behavior in Solutions. Ph.D. Dissertation, A. E. Arbuzov Institute of Organic and Physical Chemistry, Russian Federation, Kazan, 2015.
- Law, D. J. The Synthesis of Aminomethylphosphines, Their Metal Complexes and Their Use in Homogeneous Catalysis. Ph.D. Dissertation, University of Leicester, Leicester, UK, 1990.
- Bodendorf, K.; Koralewski, G. Über den Mechanismus der Kondensation zwischen Aminen, Formaldehyd und Ketonen. Arch. Pharm. Pharm. Med. Chem. 1933, 271, 101–116. DOI: https://doi.org/10.1002/ardp.19332710205.
- Petrov, K. A.; Chauzov, V. A.; Erokhina, T. S. Investigation of Interaction of Dibenzylphosphine Oxide and Dibutyl Phosphite with Formaldehyde and Diethylamine. Zh. Obshch. Khim. 1975, 45, 737–744.
- Galkin, V. I.; Zvereva, E. R.; Sobanov, A. A.; Galkina, I. V.; Cherkasov, R. A. Kinetics and Mechanism of Kabachnik–Fields Reaction in Dialkylphosphite-Benzaldehyde-Aniline System. Zh. Obshch. Khim. 1993, 63, 2224–2227.
- Keglevich, G.; Fehérvári, A.; Csontos, I. A Study on the Kabachnik–Fields Reaction of Benzaldehyde, Propylamine, and Diethyl Phosphite by in Situ Fourier Transform IR Spectroscopy. Heteroatom Chem. 2011, 22, 599–604. DOI: https://doi.org/10.1002/hc.20676.
- Keglevich, G.; Rádai, Z. α-Hydroxyphosphonates as Intermediates in the Kabachnik–Fields Reaction: New Proof of Their Reversible Formation. Tetrahedron Lett. 2020, 61, 151961. DOI: https://doi.org/10.1016/j.tetlet.2020.151961.
- Matveeva, E. D.; Zefirov, N. S. On the Mechanism of the Kabachnik-Fields Reaction: Does a Mechanism of Nucleophilic Amination of α-Hydroxyphosphonates Exist? Dokl. Chem. 2008, 420, 137–140. DOI: https://doi.org/10.1134/S0012500808060037.
- Swor, C. D.; Hanson, K. R.; Zakharov, L. N.; Tyler, D. R. Reactions of Coordinated Hydroxymethylphosphines with NH-Functional Amines: The Phosphorus Lone Pair is Crucial for the Phosphorus Mannich Reaction. Dalton Trans. 2011, 40, 8604–8610. doi: https://doi.org/10.1039/C1DT10586H.
- Lach, J. α-Phosphanyl-α-Aminosäuren: Synthese, Struktur, Eigenschaften und Reaktivität unterschiedlich N-substituierter phosphanylglycine. Ph.D. Dissertation, University of Greifswald, Greifswald, Germany, 2009.
- Petrov, K. A.; Chauzov, V. A.; Erokhina, T. S. Interactions in Dibenzylphosphine Oxide-Formaldehyde-Aniline System; Replacement of the Hydroxy Group of (Hydroxymethyl) Phosphonic Acid with Amino Group. Khim. Elementoorg. Soedin. 1976, 200–204.
- Gancarz, R.; Gancarz, I.; Walkowiak, U. On the Reversibility of Hydroxyphosphonate Formation in the Kabachnik-Fields Reaction. Phosphorus Sulfur Silicon Relat. Elem. 1995, 104, 45–52. DOI: https://doi.org/10.1080/10426509508042576.
- Cytlak, T.; Skibińska, M.; Kaczmarek, P.; Kaźmierczak, M.; Rapp, M.; Kubicki, M.; Koroniak, H. Functionalization of α-Hydroxyphosphonates as a Convenient Route to N-Tosyl-α-Minophosphonates. RSC Adv. 2018, 8, 11957–11974. DOI: https://doi.org/10.1039/C8RA01656A.
- Reimers, J. R.; McKemmish, L. K.; McKenzie, R. H.; Hush, N. S. Bond Angle Variations in XH3 [X = N, P, as, Sb, Bi]: the Critical Role of Rydberg Orbitals Exposed Using a Diabatic State Model. Phys. Chem. Chem. Phys. 2015, 17, 24618–24640. DOI: https://doi.org/10.1039/C5CP02237A.
- Ikuta, S.; Kebarle, P. A Comparison of Methyl and Phenyl Substituent Effects on the Gas Phase Basicities of Amines and Phosphines. Can. J. Chem. 1983, 61, 97–102. DOI: https://doi.org/10.1139/v83-017.
- Grinshtein, E. I.; Bruker, A. B.; Soborovskii, L. Z. Hydroxymethylation of Phosphine and Its Derivatives. Dokl. Akad. Nauk SSSR 1961, 139, 1359–1362.
- Bruker, A. B.; Baranaev, M. K.; Grinshtein, E. I.; Novoselova, R. I.; Prokhorova, V. V.; Soborovskii, L. Z. Mechanism and Kinetics of Phosphine Hydroxymethylation. Zh. Obshch. Khim. 1963, 33, 1919–1923.
- Henderson, W. A.; Buckler, S. A. The Nucleophilicity of Phosphines. J. Am. Chem. Soc. 1960, 82, 5794–5800. DOI: https://doi.org/10.1021/ja01507a009.
- Heo, C. K. M.; Bunting, J. W. Nucleophilicity towards a Vinylic Carbon Atom: Rate Constants for the Addition of Amines to the 1-Methyl-4-Vinylpyridinium Cation in Aqueous Solution. J. Chem. Soc. Perkin Trans. 2. 1994, 2279–2290. DOI: https://doi.org/10.1039/p29940002279.
- Bunting, J. W.; Mason, J. M.; Heo, C. K. M. Nucleophilicity towards a Saturated Carbon Atom: Rate Constants for the Aminolysis of Methyl 4-Nitrobenzenesulfonate in Aqueous Solution. A Comparison of the n and N+ Parameters for Amine Nucleophilicity. J. Chem. Soc. Perkin Trans. 2. 1994, 2291–2300. DOI: https://doi.org/10.1039/p29940002291.
- Mayr, H.; Ofial, A. R. Kinetics of Electrophile-Nucleophile Combinations: A General Approach to Polar Organic Reactivity. Pure Appl. Chem. 2005, 77, 1807–1821. DOI: https://doi.org/10.1351/pac200577111807.
- Brotzel, F.; Chu, Y. C.; Mayr, H. Nucleophilicities of Primary and Secondary Amines in Water. J. Org. Chem. 2007, 72, 3679–3688. DOI: https://doi.org/10.1021/jo062586z.
- Mayr, H.; Ofial, A. R. Do General Nucleophilicity Scales Exist? J. Phys. Org. Chem. 2008, 21, 584–595. DOI: https://doi.org/10.1002/poc.1325.
- Kanzian, T.; Nigst, T. A.; Maier, A.; Pichl, S.; Mayr, H. Nucleophilic Reactivities of Primary and Secondary Amines in Acetonitrile. Eur. J. Org. Chem. 2009, 6379–6385. DOI: https://doi.org/10.1002/ejoc.200900925.
- Ammer, J.; Baidya, M.; Kobayashi, S.; Mayr, H. Nucleophilic Reactivities of Rertiary Alkylamines. J. Phys. Org. Chem. 2010, 23, 1029–1035. DOI: https://doi.org/10.1002/poc.1707.
- Davies, W. C.; Lewis, W. P. G. Factors Affecting -Onium Salt Formation. J. Chem. Soc. 1934, 1599–1604. DOI: https://doi.org/10.1039/jr9340001599.
- Kren, R. M.; Sisler, H. H. Relative Reactivity of Phosphines and Amines toward Chloramines and Methyl Iodide. Inorg. Chem. 1970, 9, 836–839. DOI: https://doi.org/10.1021/ic50086a029.
- Ghazy, T.; Kane-Maguire, L. A. P. Kinetics of Nucleophilic Attack on Coordinated Organic Moieties: XXVI. An Extended Nucleophilicity Scale for Nucleophilic Addition to the Cation [Fe(CO)3(1-5-η-C6H7)]+. J. Organomet. Chem. 1980, 338, 47–53. DOI: https://doi.org/10.1016/0022-328X(80)83006-3.
- Bunton, C. A.; Huang, S. K. Reactions of the Tri-p-Anisylmethyl Cation with Primary and Secondary Amines. J. Am. Chem. Soc. 1974, 96, 515–522. DOI: https://doi.org/10.1021/ja00809a029.
- Issleib, K.; Kühne, U.; Krech, F. 1,5-Aza-Phosphabicyclo[3.2.1] octan—Bildung und Reaktionsverhalten. Z. Anorg. Allg. Chem. 1985, 523, 7–13. DOI: https://doi.org/10.1002/zaac.19855230402.
- Stewart, R.; Harris, M. G. Comparison of the Acidities and Basicities of Amino-Substituted Nitrogen Heterocycles. J. Org. Chem. 1978, 43, 3123–3126. DOI: https://doi.org/10.1021/jo00410a006.
- Alternative Sites of Protonation and Deprotonation. In The Proton: Applications to Organic Chemistry; Stewart, R., Ed.; Academic Press: Orlando, FL, 1985; Vol. 46, pp 185–216. DOI: https://doi.org/10.1016/B978-0-12-670370-2.50009-8.[101]
- Ben-Aroya, B. B.-N.; Portnoy, M. Solid-Phase Synthesis of an α-aminophosphine library. J. Comb. Chem. 2001, 3, 524–527. DOI: https://doi.org/10.1021/cc0100363.
- Stephan, G. C.; Näther, C.; Sivasankar, C.; Tuczek, F. Mo– and W–N2 and –CO Complexes with Novel Mixed P/N Ligands: Structural Properties and Implications to Synthetic Nitrogen Fixation. Inorg. Chim. Acta. 2008, 361, 1008–1019. DOI: https://doi.org/10.1016/j.ica.2007.06.046.
- Kempf, B.; Mayr, H. Rates and Equilibria of the Reactions of Tertiary Phosphanes and Phosphites with Benzhydrylium Ions. Chemistry 2005, 11, 917–927. DOI: https://doi.org/10.1002/chem.200400696.
- Atton, J. G.; Kane-Maguire, L. A. P. Kinetics of Nucleophilic Attack on Coordinated Organic Moieties. Part 21. Factors Governing the Nucleophilicity of Phosphorus Nucleophiles towards [Fe(CO)3(1–5-η-C6H7)]+. J. Chem. Soc., Dalton Trans. 1982, 1491–1498. DOI: https://doi.org/10.1039/DT9820001491.
- Albert, A.; Goldacre, R.; Phillips, J. The Strength of Heterocyclic Bases. J. Chem. Soc. 1948, 2240–2249. DOI: https://doi.org/10.1039/jr9480002240.
- Richmond, H. H.; Myers, G. S.; Wright, G. F. The Reaction between Formaldehyde and Ammonia. J. Am. Chem. Soc. 1948, 70, 3659–3664. DOI: https://doi.org/10.1021/ja01191a034.
- Ogata, Y.; Kawasaki, A. The Kinetics of the Reaction of Formaldehyde with Ammonia. Bull. Chem. Soc. Jpn. 1964, 37, 514–519. DOI: https://doi.org/10.1246/bcsj.37.514.
- Nielsen, A. T.; Moore, D. W.; Ogan, M. D.; Atkins, R. L. Structure and Chemistry of the Aldehyde Ammonias. 3. Formaldehyde-Ammonia Reaction. 1,3,5-Hexahydrotriazine. J. Org. Chem. 1979, 44, 1678–1684. DOI: https://doi.org/10.1021/jo01324a021.
- Zeffiro, A.; Lazzaroni, S.; Merli, D.; Profumo, A.; Buttafava, A.; Serpone, N.; Dondi, D. Formation of Hexamethylenetetramine (HMT) from HCHO and NH3 – Relevance to Prebiotic Chemistry and B3LYP Consideration. Orig. Life. Evol. Biosph. 2016, 46, 223–231. DOI: https://doi.org/10.1007/s11084-015-9479-5.
- Moioli, E.; Schmid, L.; Wasserscheid, P.; H, F. pH Effects in the Acetaldehyde–Ammonia Reaction. React. Chem. Eng. 2017, 2, 382–389. DOI: https://doi.org/10.1039/C7RE00006E.
- Tuguldurova, V. P.; Fateev, A. V.; Malkov, V. S.; Poleshchuk, O. K.; Vodyankina, O. V. Acetaldehyde-Ammonia Interaction: A DFT Study of Reaction Mechanism and Product Identification. J. Phys. Chem. A. 2017, 121, 3136–3141. DOI: https://doi.org/10.1021/acs.jpca.7b00823.
- Wagner, E. C. A Rationalization of Acid-Induced Reactions of Methylene-bis-Amines, Methylene-Amines, and of Formaldehyde and Amines. J. Org. Chem. 1954, 19, 1862–1881. DOI: https://doi.org/10.1021/jo01377a002.
- Kallen, R. G.; Jencks, W. P. Equilibria for the Reaction of Amines with Formaldehyde and Protons in Aqueous Solution. J. Biol. Chem. 1966, 241, 5864–5878. DOI: https://doi.org/10.1016/S0021-9258(18)96351-9.
- Jencks, W. P. Mechanism and Catalysis of Simple Carbonyl Group Reactions. In Progress in Physical Organic Chemistry; Cohen, S. G., Streitwieser, A., Taft, R. W., Eds.; John Wiley & Sons: New York, 1964; Vol. 2, pp 63–128. DOI: https://doi.org/10.1002/9780470171813.ch2.
- Hine, J.; Via, F. A. Kinetics of the Formation of Imines from Isobutyraldehyde and Primary Aliphatic Amines with Polar Substituents. J. Am. Chem. Soc. 1972, 94, 190–194. DOI: https://doi.org/10.1021/ja00756a033.
- Abrams, W. R.; Kallen, R. G. Equilibria and Kinetics of N-Hydroxymethylamine Formation from Aromatic Exocyclic amines and Formaldehyde. Effects of Nucleophilicity and Catalyst Strength upon Mechanisms of Catalysis of Carbinolamine Formation. J. Am. Chem. Soc. 1976, 98, 7777–7789. DOI: https://doi.org/10.1021/ja00440a052.
- Sayer, J. M.; Conlon, P. The Timing of the Proton-Transfer Process in Carbonyl Additions and Related Reactions. General-Acid-Catalyzed Hydrolysis of Imines and N-Acylimines of Benzophenone. J. Am. Chem. Soc. 1980, 102, 3592–3600. DOI: https://doi.org/10.1021/ja00530a046.
- Verardo, G.; Gorassini, F.; Giumanini, A. G.; Scubla, T.; Tolazzi, M.; Strazzolini, P. Heteroaromatic Primary Amines and Formaldehyde: The Formation of N-Hydroxymethyl Derivatives. Tetrahedron 1995, 51, 8311–8322. DOI: https://doi.org/10.1016/0040-4020(95)00442-B.
- Wan, Y.; Yuan, R.; Zhang, W.; Shi, Y.; Lin, W.; Yin, W.; Bo, R.; Shi, J.; Wu, H. Two Isolated Intermediates of the Tröger's Base: Synthesis and Mechanism. Tetrahedron 2010, 66, 3405–3409. DOI: https://doi.org/10.1016/j.tet.2010.03.057.
- Jones, G. O.; García, J. M.; Horn, H. W.; Hedrick, J. L. Computational and Experimental Studies on the Mechanism of Formation of Poly(Hexahydrotriazine)s and Poly(Hemiaminal)s from the Reactions of Amines with Formaldehyde. Org. Lett. 2014, 16, 5502–5505. DOI: https://doi.org/10.1021/ol502840k.
- Ciaccia, M.; Stefano, S. Mechanisms of Imine Exchange Reactions in Organic Solvents. Org. Biomol. Chem. 2015, 13, 646–654. DOI: https://doi.org/10.1039/C4OB02110J.
- Rogers, F. E.; Rapiejko, R. J. Thermochemistry of Carbonyl Addition Reactions. II. Enthalpy of Addition of Dimethylamine to Formaldehyde. J. Phys. Chem. 1974, 78, 599–603. DOI: https://doi.org/10.1021/j100599a008.
- Hine, J.; Kokesh, F. C. Rate and Equilibrium Constants for Each Step in the Reaction of Trimethylammonium Ions with Formaldehyde to Give Formocholine Cations in Aqueous Solution. J. Am. Chem. Soc. 1970, 92, 4383–4388. DOI: https://doi.org/10.1021/ja00717a040.
- Stewart, T. D.; Kung, H. P. The Preparation and the Quaternary Ammonium Decomposition of Formocholine. J. Am. Chem. Soc. 1933, 55, 4813–4819. DOI: https://doi.org/10.1021/ja01339a011.
- Kirby, A. J.; Komarov, I. V.; Bilenko, V. A.; Davies, J. E.; Rawson, J. M. Structure and Chemistry of a Zwitterionic Amine–Aldehyde Adduct. Chem. Commun. 2002, 2106–2107. DOI: https://doi.org/10.1039/B206639D.
- Mathes, N.; Jaacks, V. On the Mechanism of Polymerization of Formaldehyde Initiated by Tertiary Amines and Phosphines. Makromol. Chem. 1970, 135, 49–67. DOI: https://doi.org/10.1002/macp.1970.021350106.
- Diebler, H.; Thorneley, R. N. F. Kinetics of Carbonyl Addition Reactions. I. Temperature-Jump Study of Carbinolamine Formation between Piperazine and Pyridine-4-Aldehyde. J. Am. Chem. Soc. 1973, 95, 896–904. DOI: https://doi.org/10.1021/ja00784a044.
- Sayer, J. M.; Peskin, M.; Jencks, W. P. Imine-Forming Elimination Reactions. I. General Base Acid Catalysis and Influence of the Nitrogen Substituent on Rates and Equilibria for Carbinolamine Dehydration. J. Am. Chem. Soc. 1973, 95, 4277–4287. DOI: https://doi.org/10.1021/ja00794a600.
- Sayer, J. M.; Edman, C. The Timing of the Proton Transfer Process in Acid-Catalyzed Carbonyl Addition. Evidence for a Preassociation Mechanism for Catalysis of Carbinolamine Formation from Acethydrazide and p-Chlorobenzaldehyde. J. Am. Chem. Soc. 1979, 101, 3010–3016. DOI: https://doi.org/10.1021/ja00505a031.
- Böhme, H.; Mundlos, E.; Herboth, O. E. Über Darstellung und Eigenschaften α‐Halogenierter Amine. Chem. Ber. 1957, 90, 2003–2008. DOI: https://doi.org/10.1002/cber.19570900942.
- Böhme, H.; Lehners, W.; Keitzer, G. Über α-Halogenierte Amine, III. Über die Spaltung von Diamino-methan-Derivaten mit Halogenwasserstoffen. Chem. Ber. 1958, 91, 340–345. DOI: https://doi.org/10.1002/cber.19580910218.
- Appel, R.; Chelli, S.; Tokuyasu, T.; Troshin, K.; Mayr, H. Electrophilicities of Benzaldehyde-Derived Iminium Ions: Quantification of the Electrophilic Activation of Aldehydes by Iminium Formation. J. Am. Chem. Soc. 2013, 135, 6579–6587. DOI: https://doi.org/10.1021/ja401106x.
- Appel, R.; Mayr, H. Quantification of the Electrophilic Reactivities of Aldehydes, Imines, and Enones. J. Am. Chem. Soc. 2011, 133, 8240–8251. DOI: https://doi.org/10.1021/ja200820m.
- Layer, R. W. The Chemistry of Imines. Chem. Rev. 1963, 63, 489–510. DOI: https://doi.org/10.1021/cr60225a003.
- Robertson, G. M. Imines and Their N-Substituted Derivatives: NH, NR and N-Haloimines. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon, 1995; Vol. 3, pp 403–423. DOI: https://doi.org/10.1016/B0-08-044705-8/00170-9.
- Patil, R. D.; Adimurthy, S. Catalytic Methods for Imine Synthesis. Asian J. Org. Chem 2013, 2, 726–744. DOI: https://doi.org/10.1002/ajoc.201300012.
- Böhme, H.; Ellenberg, H. Über α‐Halogenierte Amine, VII. Über Die Spaltung von α‐Dialkylamino‐Äthern mit Halogenwasserstoffen. Chem. Ber. 1959, 92, 2976–2981. DOI: https://doi.org/10.1002/cber.19590921148.
- Böhme, H.; Hartke, K. Über α‐halogenierte Amine, VIII. Über die Spaltung von Aminalen und α‐Dialkylamino‐Äthern mit Carbonsäurehalogeniden. Chem. Ber. 1960, 93, 1305–1309. DOI: https://doi.org/10.1002/cber.19600930610.
- Schreiber, J.; Maag, H.; Hashimoto, N.; Eschenmoser, A. Dimethyl(Methylene)Ammonium Iodide. Angew. Chem. Int. Ed. Engl. 1971, 10, 330–331. DOI: https://doi.org/10.1002/anie.197103301.
- Bryson, T. A.; Bonitz, G. H.; Reichel, C. J.; Dardis, R. E. Performed Mannich Salts: A Facile Preparation of Dimethyl(Methylene)Ammonium Iodide. J. Org. Chem. 1980, 45, 524–525. DOI: https://doi.org/10.1021/jo01291a032.
- Rochin, C.; Babot, O.; Dunoguès, J.; Duboudin, F. A New Convenient Synthesis of Dialkyl(Methylene)Ammonium Chloride. Synthesis 1986, 1986, 228–229. DOI: https://doi.org/10.1055/s-1986-31627.
- Schroth, W.; Jahn, U. Erzeugung von N,N‐Disubstituierten Iminiumsalzen mit Hilfe von Silan‐Reagenzien. J. Prakt. Chem. 1998, 340, 287–299. DOI: https://doi.org/10.1002/prac.19983400402.
- McLeod, C. M.; Robinson, G. M. Researches on Pseudo-Bases. Part III. Dialkylaminomethyl Alkyl Ethers and Sulphides. J. Chem. Soc., Trans 1921, 119, 1470–1476. DOI: https://doi.org/10.1039/CT9211901470.
- Grillot, G. F.; Felton, H. R.; Garrett, B. R.; Greenberg, H.; Green, R.; Clementi, R.; Moskowitz, M. The Condensation of Thiophenols with Secondary Amines and Formaldehyde. J. Am. Chem. Soc. 1954, 76, 3969–3971. DOI: https://doi.org/10.1021/ja01644a030.
- Tramontini, M.; Angiolini, L. Further Advances in the Chemistry of Mannich Bases. Tetrahedron 1990, 46, 1791–1837. DOI: https://doi.org/10.1016/S0040-4020(01)89752-0.
- Hellmann, H.; Bader, J.; Birkner, H.; Schumacher, O. Hydroxymethyl-Phosphine, Hydroxymethyl-Phosphoniumsalze und Chloromethyl-Phosphoniumsalze. Justus Liebigs Ann. Chem. 1962, 659, 49–63. DOI: https://doi.org/10.1002/jlac.19626590107.
- Märk, G.; Jin, G. Y. N. N.N-Tris[Phosphinomethylen]Amine N.N.N′-Tris[Phosphinomethylen]Hydrazine N.N.N′.N′-Tetra [Phosphinomethylen]Hydrazine. Tetrahedron Lett. 1981, 22, 1105–1108. DOI: https://doi.org/10.1016/S0040-4039(01)90248-5.
- Muller, G.; Sainz, D. Synthesis of Monohydroxy -Methyl- and -Ethyl-Phosphines PPh2CHROH. J. Organomet. Chem. 1995, 495, 103–111. DOI: https://doi.org/10.1016/0022-328X(95)05425-O.
- Moiseev, D. V.; Marcazzan, P.; James, B. R. Reversible Decomposition of Mono(α-Hydroxy)Phosphines and Their Reaction with α,β-Unsaturated Aldehydes. Can. J. Chem. 2009, 87, 582–590. DOI: https://doi.org/10.1139/V09-021.
- Moiseev, D. V.; Patrick, B. O.; James, B. R. New Tertiary Phosphines from Cinnamaldehydes and Diphenylphosphine. Inorg. Chem. 2007, 46, 11467–11474. DOI: https://doi.org/10.1021/ic701597g.
- Fawcett, J.; Hoye, P. A. T.; Kemmitt, R. D. W.; Law, D. J.; Russell, D. R. Synthesis of Bis(Phosphinomethyl)Amines via Bis(Hydroxymethyl)Phosphonium Salts. Isolation of 9,9-Bis(Hydroxymethyl)-9-Phosphoniabicyclo[3.3.1]Nonane Hydrogensulfate and Chloride Salts, and the Crystal Structures of [PPh2(CH2OH)2]+Cl– and [(C6H11)2PCH2]2NCHMePh. J. Chem. Soc. Dalton Trans. 1993, 2563–2568. DOI: https://doi.org/10.1039/dt9930002563.
- Lee, S. W.; Trogler, W. C. Nucleophilic Addition of Phosphines to Carbonyl Groups. Isolation of 1-Hydroxy Phosphonium and 1-(Trimethylsiloxy) Phosphonium Salts and the Crystal Structure of (1-Hydroxy-1-Methylethyl)Triethylphosphonium Bromide. J. Org. Chem. 1990, 55, 2644–2648. DOI: https://doi.org/10.1021/jo00296a020.
- Canto, R. A. D.; Roskamp, E. J. Addition of Triphenylphosphonium Salts to Aldehydes. Remarkable Counterion Effects on Phosphorus Proton Couplings. J. Org. Chem. 1992, 57, 406–407. DOI: https://doi.org/10.1021/jo00027a077.
- Darensbourg, D. J.; Joo, F.; Katho, A.; Stafford, J. N. W.; Benyei, A.; Reibenspies, J. H. Nucleophilic Addition of a Water-Soluble Phosphine to Aldehydes. Isolation of (1-Hydroxyalkyl) Phosphonium Salts and the Crystal Structure of the (1-Methoxy-1-Benzyl)(m-Sulfonatophenyl)Diphenylphosphonium Salt. Inorg. Chem. 1994, 33, 175–177. DOI: https://doi.org/10.1021/ic00079a031.
- Moiseev, D. V.; James, B. R.; Hu, T. Q. Alpha-Monodeuterated Benzyl Alcohols and Phosphobetaines from Reactions of Aromatic Aldehydes with a Water/D2O-soluble Phosphine. Inorg. Chem. 2006, 45, 10338–10346. DOI: https://doi.org/10.1021/ic0613560.
- Westhues, N.; Klankermayer, J. Transfer Hydrogenation of Carbon Dioxide to Methanol Using a Molecular Ruthenium-Phosphine Catalyst. Chem. Cat. Chem 2019, 11, 3371–3375. DOI: https://doi.org/10.1002/cctc.201900932.
- Phanopoulos, A.; Brown, N. J.; White, A. J. P.; Long, N. J.; Miller, P. W. Synthesis, Characterization, and Reactivity of Ruthenium Hydride Complexes of N-Centered Triphosphine Ligands. Inorg. Chem. 2014, 53, 3742–3752. DOI: https://doi.org/10.1021/ic500030k.
- Scherl, P.; Kruckenberg, A.; Mader, S.; Wadepohl, H.; Gade, L. H. Ruthenium η4-Trimethylenemethane Complexes Containing Tripodal Phosphanomethylamine Ligands. Organometallics 2012, 31, 7024–7027. DOI: https://doi.org/10.1021/om300794h.
- Deng, L.; Kang, B.; Englert, U.; Klankermayer, J.; Palkovits, R. Direct Hydrogenation of Biobased Carboxylic Acids Mediated by a Nitrogen-Centered Tridentate Phosphine Ligand. ChemSusChem 2016, 9, 177–180. DOI: https://doi.org/10.1002/cssc.201501461.
- Westhues, N.; Belleflamme, M.; Klankermayer, J. Base-Free Hydrogenation of Carbon Dioxide to Methyl Formate with a Molecular Ruthenium-Phosphine Catalyst. ChemCatChem 2019, 11, 5269–5274. DOI: https://doi.org/10.1002/cctc.201900627.
- Phanopoulos, A.; Nozaki, K. Branched-Selective Hydroformylation of Nonactivated Olefins Using an N-Triphos/Rh Catalyst. ACS Catal. 2018, 8, 5799–5809. DOI: https://doi.org/10.1021/acscatal.8b00566.
- Siebert, M.; Seibicke, M.; Siegle, A. F.; Kräh, S.; Trapp, O. Selective Ruthenium-Catalyzed Transformation of Carbon Dioxide: An Alternative Approach toward Formaldehyde. J. Am. Chem. Soc. 2019, 141, 334–341. DOI: https://doi.org/10.1021/jacs.8b10233.
- Fillol, J. L.; Kruckenberg, A.; Scherl, P.; Wadepohl, H.; Gade, L. H. Stitching Phospholanes Together Piece by Piece: New Modular Di- and Tridentate Stereodirecting Ligands. Chemistry 2011, 17, 14047–14062. DOI: https://doi.org/10.1002/chem.201101864.
- Huang, W.; Rong, H.-Y.; Xu, J. Cyclic α-Alkoxyphosphonium Salts from (2-(Diphenylphosphino)Phenyl)Methanol and Aldehydes and Their Application in Synthesis of Vinyl Ethers and Ketones via Wittig Olefination. J. Org. Chem. 2015, 80, 6628–6638. DOI: https://doi.org/10.1021/acs.joc.5b01031.
- Issleib, K.; Oehme, H.; Kümmel, R.; Leißring, E. 1,3-Azaphospholidine. Chem. Ber. 1968, 101, 3619–3622. DOI: https://doi.org/10.1002/cber.19681011036.
- Röschenthaler, G.-V. Über die Insertion von Hexafluoraceton in P-H-Bindungen von Phosphanen MenPH3-n. Z. Naturforsch. 1978, 33B, 311–315.
- Evangelidou-Tsolis, E.; Ramirez, F.; Pilot, J. F.; Smith, C. P. Reactions of Secondary and Tertiary Phosphines with Monocarbonyl Compounds. Phosphorus 1974, 5, 109–119. DOI: https://doi.org/10.1002/chin.197448406.
- Peulecke, N.; Kindermann, M. K.; Köckerling, M.; Heinicke, J. Phosphonium Bis(Glycolates) and Phosphinoglycolates: Synthesis, Solvolysis, Oxidation to (Thio)Phosphinoylglycolates and Use as Ligands in Ni-Catalyzed Ethylene Oligomerization. Polyhedron 2012, 41, 61–69. DOI: https://doi.org/10.1016/j.poly.2012.04.019.
- Moiseev, D. V.; James, B. R.; Gushchin, A. V. Interaction of PH3 with Acetaldehyde in Aqueous Media and Chemistry of [HO(Me)CH]4PCl. Russ. J. Gen. Chem. 2013, 83, 252–259. DOI: https://doi.org/10.1134/S1070363213020047.
- Muralidharan, K.; Reddy, N. D.; Elias, A. J. Syntheses of Novel Exo and Endo Isomers of Ansa-Substituted Fluorophosphazenes and Their Facile Transformations into Spiro Isomers in the Presence of Fluoride Ions. Inorg. Chem. 2000, 39, 3988–3994. DOI: https://doi.org/10.1021/ic0001863.
- Babu, H. V.; Srinivas, B.; Naik, K. P. K.; Muralidharan, K. Polymerization Behaviour of Butyl Bis(Hydroxymethyl) Phosphine Oxide: Phosphorus Containing Polyethers for Li-Ion Conductivity. J. Chem. Sci. 2015, 127, 635–641. DOI: https://doi.org/10.1007/s12039-015-0819-9.
- Ramakrishna, T. V. V.; Elias, A. J. Reactions of Ferrocene-Derived Bis(Hydroxymethyl) Phosphine Sulfides FcCH(R)P(S) (CH2OH)2 (R = H, CH3) with Cyclic Thionylphosphazenes: Crystal Structures of FcCH2P(S)(CH2O)2PN(NPCl2)[NS(O)Ph] and FcCH2P(S)(CH2O)2PN2P[N(Me)CH2]2[NS(O)Ph] (Fc = Ferrocenyl). J. Organomet. Chem. 2001, 637-639, 382–389. DOI: https://doi.org/10.1016/S0022-328X(01)00939-1.
- Le Hénaff, P. Sur Les Équilibres de Formation et la Vitesse de Décomposition des Hémiacétals et des Hémimercaptals Dérivés du Formol. C. R. Acad. Sci. Ser. C 1966, 262, 1667–1670.
- Guthrie, J. P. Carbonyl Addition Reactions: Factors Affecting the Hydrate–Hemiacetal and Hemiacetal–Acetal Equilibrium Constants. Can. J. Chem. 1975, 53, 898–906. DOI: https://doi.org/10.1139/v75-125.
- Gómez-Bombarelli, R.; González-Pérez, M.; Pérez-Prior, M. T.; Calle, E.; Casado, J. Computational Calculation of Equilibrium Constants: Addition to Carbonyl Compounds. J. Phys. Chem. A. 2009, 113, 11423–11428. DOI: https://doi.org/10.1021/jp907209a.
- Goodwin, N. J.; Henderson, W.; Nicholson, B. K. An Air-Stable, Primary Alkylphosphine: FcCH2PH2 [Fc = (η5-C5H5)Fe(η5-C5H4)]. Chem. Commun. 1997, 31–32. DOI: https://doi.org/10.1039/a606580e.
- Asamizu, T.; Henderson, W.; Nicholson, B. K.; Hey-Hawkins, E. Extending the Range of Stabilised, Primary and Secondary Phosphanes Containing Ferrocenyl or Ruthenocenyl Groups. Inorg. Chim. Acta. 2014, 414, 181–190. DOI: https://doi.org/10.1016/j.ica.2014.01.049.
- Goodwin, N. J.; Henderson, W.; Nicholson, B. K.; Fawcett, J.; Russell, D. R. (Ferrocenylmethyl)Phosphine, an Air-Stable Primary Phosphine. J. Chem. Soc. Dalton Trans. 1999, 1785–1794. DOI: https://doi.org/10.1039/a901036j.
- Pet, M. A.; Cain, M. F.; Hughes, R. P.; Glueck, D. S.; Golen, J. A.; Rheingold, A. L. Synthesis and Structure of Ferrocenylmethylphosphines, Their Borane Adducts, and Some Related Derivatives. J. Organomet. Chem. 2009, 694, 2279–2289. DOI: https://doi.org/10.1016/j.jorganchem.2009.03.015.
- Moiseev, D. V.; James, B. R.; Hu, T. Q. Characterization of Secondary and Primary (Hydroxymethyl)Phosphines and Their Oxidation Products: Synergism in Pulp-Bleaching. Phosphorus Sulfur Silicon Relat. Elem. 2012, 187, 433–447. DOI: https://doi.org/10.1080/10426507.2011.632388.
- Guthrie, J. P. Hydration of Carbonyl Compounds, an Analysis in Terms of Multidimensional Marcus Theory. J. Am. Chem. Soc. 2000, 122, 5529–5538. DOI: https://doi.org/10.1021/ja992992i.
- Kellner, K.; Seidel, B.; Tzschach, A. Organoarsen-Verbindungen: XXXIII. Synthese und Reaktionsverhalten der α-Aminomethylphosphine und -Arsine. J. Organomet. Chem. 1978, 149, 167–176. DOI: https://doi.org/10.1016/S0022-328X(00)94119-6..
- Oehme, H.; Issleib, K.; Leissring, E. 1,3-Oxaphospholane. Tetrahedron 1972, 28, 2587–2592. DOI: https://doi.org/10.1016/0040-4020(72)80093-0.
- Heinicke, J. W.; Thede, G.; Schulzke, C.; Jones, P. G.; Frauendorf, H. PH-Functional and P-(α-Hydroxy)Benzyl-2-Phenyl-1,3-Oxaphospholanes – Synthesis, Reactivity and Structural Aspects. Polyhedron 2019, 170, 731–741. DOI: https://doi.org/10.1016/j.poly.2019.06.037.
- Song, L.-C.; Tan, H.; Luo, F.-X.; Wang, Y.-X.; Ma, Z.; Niu, Z. Synthesis, Structural Characterization, and Catalytic H2 Production of Ferrocenyl (Fc) Group Containing Complexes [Ni(PFc2NAr2)2](BF4)2 (Ar = Ph, p-BrC6H4). Organometallics 2014, 33, 5246–5253. DOI: https://doi.org/10.1021/om500571n.
- Langbein, S.; Wadepohl, H.; Gade, L. H. Ditopic N-Heterocyclic Pincer Carbene Complexes Containing a Perylene Backbone. Organometallics 2016, 35, 809–815. DOI: https://doi.org/10.1021/acs.organomet.6b00049.
- Karasik, A. A.; Naumov, R. N.; Kanunnikov, K. B.; Krivolapov, D. B.; Litvinov, I. A.; Lönnecke, P.; Balueva, A. S.; Musina, E. I.; Hey-Hawkins, E.; Sinyashin, O. G. Synthesis of New Examples of Corands with 16-Membered P,N-Containing Core Ring. Macroheterocycles 2014, 7, 181–188. DOI: https://doi.org/10.6060/mhc140507b.
- Pann, J.; Ehrmann, K.; Pehn, R.; Roithmeyer, H.; Viertl, W.; Kopacka, H.; Brüggeller, P.; Oberhauser, W. Cu(I) Coordination by N,N,N’,N’-Tetra(di-ortho-Anisylphosphanylmethyl)Ethylene and Propylene Diamine: First Example of a Sandwiched CuCl-Tetramer. Inorg. Chim. Acta. 2021, 516, 120162. DOI: https://doi.org/10.1016/j.ica.2020.120162.
- Adamek, J.; Zieleźny, P.; Erfurt, K. Synthesis of N-Protected 1-Aminoalkylphosphonium Salts from Amides, Carbamates, Lactams, or Imides. J. Org. Chem. 2021, 86, 5852–5862. DOI: https://doi.org/10.1021/acs.joc.1c00285.
- Issleib, K.; Schmidt, H.; Leißring, E. Phospha-Alkenbildung durch Direkte Kondensation aus Ar-PH2 und R-CHO. Z. Chem. 2010, 26, 406–407. DOI: https://doi.org/10.1002/zfch.19860261114.
- Romanenko, V. D.; Ruban, A. V.; Povolotskii, M. I.; Polyachenko, L. K.; Markovskii, L. N. Synthesis of Phosphaalkenes by Reaction of (2,4,6-Tri-tert-Butylphenyl)Phosphine with Carbonyl Compounds. Zh. Obshch. Khim. 1986, 56, 1186–1187.
- Romanenko, V. D.; Ruban, A. V.; Chernega, A. N.; Povolotskii, M. I.; Antipin, M. Y.; Struchkov, Y. T.; Markovskii, L. N. Direct Synthesis of Phosphaalkens by Reaction of (2,4,6-Tri-tert-Butylphenyl)Phosphine with Carbonyl Compounds. Zh. Obshch. Khim. 1989, 59, 1718–1725.
- Grützmacher, H.; Marchand, C. M. Heteroatom Stabilized Carbenium Ions. Coord. Chem. Rev. 1997, 163, 287–344. DOI: https://doi.org/10.1016/S0010-8545(97)00043-X.
- Floch, P. Phosphaalkene, Phospholyl and Phosphinine Ligands: New Tools in Coordination Chemistry and Catalysis. Coord. Chem. Rev. 2006, 250, 627–681. DOI: https://doi.org/10.1016/j.ccr.2005.04.032.
- Gaumont, A.-C.; Pellerin, B.; Cabioch, J.-L.; Morise, X.; Lesvier, M.; Savignac, P.; Guenot, P.; Denis, J.-M. Dehydrochlorination of α-Chlorophosphines, a Simple and General Route to Phosphaalkenes. Inorg. Chem. 1996, 35, 6667–6675. DOI: 10.1021ic960417z.
- Van Der Knaap, T. A.; Klebach, T. C.; Visser, F.; Lourens, R.; Bickelhaupt, F. [4 + 2]Cycloaddition Reactions of Triarylphosphaalkene. Tetrahedron 1984, 40, 991–997. DOI: https://doi.org/10.1016/S0040-4020(01)91236-0.
- Quin, L. D.; Tang, J.-S.; Keglevich, G. Diels-Alder Adducts of 4-Chloro-1,6-Dihydrophosphinine Derivatives: A New Precursor of 2-Phosphapropene. Heteroat. Chem. 1991, 2, 283–295. DOI: https://doi.org/10.1002/hc.520020210.
- Bansal, R. K.; Gupta, N.; Heinicke, J.; Nikonov, G. N.; Saguitova, F.; Sharma, D. C. 1H-1,3-Benzazaphospholes: The Organometallic Route and a New Three-Step Synthesis with Reductive Ring Closure. Synthesis 1999, 264–269. DOI: https://doi.org/10.1055/s-1999-3394.
- Aluri, B. R.; Jones, P. G.; Dix, I.; Heinicke, J. W. π-Excess σ2 P,O Hybrid Ligands: Synthesis of the First 4-Methoxy-1H-1,3-Benzazaphospholes. Synthesis 2014, 46, 1773–1778. DOI: https://doi.org/10.1055/s-0033-1341225.
- Niaz, B.; Aluri, B. R.; Jones, P. G.; Heinicke, J. W. π-Excess σ2P = C–N–Heterocycles: Catalytic P-Arylation and Alkylation of N-Alkyl-1,3-Benzazaphospholes and Isolation of P,N-Disubstituted Dihydrobenzazaphosphole P-Oxides. Eur. J. Inorg. Chem. 2015, 3995–4005. DOI: https://doi.org/10.1002/ejic.201500532.
- Mai, J.; Arkhypchuk, A. I.; Gupta, A. K.; Ott, S. Reductive Coupling of Two Aldehydes to Unsymmetrical E-Alkenes via Phosphaalkene and Phosphinate Intermediates. Chem Commun. 2018, 54, 7163–7166. DOI: https://doi.org/10.1039/C8CC04218G.
- Heinicke, J. W. P=C–N and P–C = N Type 1,3-Azaphospholes—Comparing the Chemistry of π-Excess Aromatic 1H- and Non-Aromatic 3H-Isomers and the Influence of Anellation (a Personal account). Phosphorus Sulfur Silicon Relat. Elem. 2019, 194, 401–409. DOI: https://doi.org/10.1080/10426507.2018.1528259.
- Aluri, B. R.; Ghalib, M.; Jones, P. G.; Frauendorf, H.; Heinicke, J. W. Synthesis of N,P-Disecondary o-Arylphosphanylanilines via o-R1NHC6H4P(R)O2Et Precursors and Preliminary Study of Cyclocondensations with (EtO)3CH/NH4PF6. Eur. J. Inorg. Chem. 2020, 182–190. DOI: https://doi.org/10.1002/ejic.201901069.
- Klebach, T.; Lourens, C. R.; Bickelhaupt, F. Synthesis of Mesityldiphenylmethylenephosphine: A Stable Compound with a Localized P = C Bond. J. Am. Chem. Soc. 1978, 100, 4886–4888. DOI: https://doi.org/10.1021/ja00483a041.
- Appel, R.; Kündgen, U. Ph(Me3Si)C = PCl as Educt for Methylenephosphanes with Alkyl-, Amino-, Phosphino-, Alkoxy-, or Alkylthio-Groups on Phosphorus. Angew. Chem. Int. Ed. 1982, 21, 219–220. DOI: https://doi.org/10.1002/anie.198202192.
- Meriem, A.; Majoral, J.-P.; Revel, M.; Navech, J. Photochemical Reactions of Phosphaalkenes. Tetrahedron Lett. 1983, 24, 1975–1978. DOI: https://doi.org/10.1016/S0040-4039(00)81820-1.
- Xie, Z.-M.; Wisian-Neilson, P.; Neilson, R. H. Synthesis and Reactivity of [Bis(Trimethylsilyl)Methylene]Mesitylphosphine. Organometallics 1985, 4, 339–344. DOI: https://doi.org/10.1021/om00121a025.
- Denis, J. M.; Guillemin, J. C.; Le Guennec, M. Synthesis of Primary α,α′-Dichlorophosphines, Precursors of Unhindered C-Chlorophospha-Alkenes and Synthetic Equivalents of λ3-Phospha-Alkynes. Phosphorus Sulfur Silicon Relat. Elem. 1990, 49-50, 317–320. DOI: https://doi.org/10.1080/10426509008038969.
- Haszeldine, R. N.; Taylor, D. R.; White, E. W. Organophosphorus Chemistry. Part 20. Reactions of Phenyltetrafluoroethylphosphine with Ammonia and Alkyl Amines: Evidence for Intermediate Phospha-Alkenes. J. Fluorine Chem. 1978, 11, 441–454. DOI: https://doi.org/10.1016/S0022-1139(00)82458-6.
- Worch, J. C.; Hellemann, E.; Pros, G.; Gayathri, C.; Pintauer, T.; Gil, R. R.; Noonan, K. J. T. Stability and Reactivity of 1,3-Benzothiaphosphole: Metalation and Diels–Alder Chemistry. Organometallics 2015, 34, 5366–5373. DOI: https://doi.org/10.1021/acs.organomet.5b00583.
- Li, B. L.; Neilson, R. H. Preparation of Phosphorus-Nitrogen-Hydrogen and Phosphorus-Phosphorus Compounds from a Silylated Amino(Methylene)Phosphine. Inorg. Chem. 1986, 25, 358–360. DOI: https://doi.org/10.1021/ic00223a026.
- Trippett, S. The Rearrangement of 1-Hydroxyalkylphosphines to Alkylphosphine Oxides. J. Chem. Soc. 1961, 2813–2816. DOI: https://doi.org/10.1039/jr9610002813.
- Buckler, S. A.; Epstein, M. Reactions of Phosphine with Ketones: A Route to Primary Phosphine Oxides. Tetrahedron 1962, 18, 1211–1219. DOI: https://doi.org/10.1016/0040-4020(62)80002-7.
- Burg, A. B.; Slota, P. J. Dimethylaminodimethylphosphine. J. Am. Chem. Soc. 1958, 80, 1107–1109. DOI: https://doi.org/10.1021/ja01538a023.
- Priya, S.; Balakrishna, M. S.; Mague, J. T.; Mobin, S. M. Insertion of Carbon Fragments into P(III)-N Bonds in Aminophosphines and Aminobis(phosphines): Synthesis, Reactivity, and Coordination Chemistry of Resulting Phosphine Oxide Derivatives. Crystal and Molecular Structures of (Ph2P(O)CH2)2NR (R = Me, nPr, nBu), Ph2P(O)CH(OH)nPr, and cis-[MoO2Cl2((Ph2P(O)CH2)2NEt-κO,κO)]}]. Inorg. Chem. 2003, 42, 1272–1281. DOI: https://doi.org/10.1021/ic026118t.
- Priya, S.; Balakrishna, M. S.; Mague, J. T. First Examples of Methylene Insertion into the Phosphorus(III)–Nitrogen Bond. Inorg. Chem. Commun. 2001, 4, 437–440. DOI: https://doi.org/10.1016/S1387-7003(01)00222-2.
- Priya, S.; Balakrishna, M. S.; Mobin, S. M. Reactions of Aminophosphines and Aminobis(Phosphines) with Aldehydes and Ketones: Coordination Complexes of the Resultant Aminobis(Alkylphosphineoxides) with Cobalt, Uranium, Thorium and Gadolinium Salts: Crystal and Molecular Structures of Ph2P(O)CH(C6H4OH-o)N(H)Ph, Ph2P(O)CH(OH) C6H4OH-o and Ph2P(O)N(H)Ph. Polyhedron 2005, 24, 1641–1650. DOI: https://doi.org/10.1016/j.poly.2005.04.036.
- Chandrasekaran, P.; Mague, J. T.; Balakrishna, M. S. Methylene Insertion into the Exocyclic P–N Bonds of Bis(Amido)Cyclodiphosphazane, cis-[tBu(H)NP(μ-tBuN)]2. Tetrahedron Lett. 2007, 48, 5227–5229. DOI: https://doi.org/10.1016/j.tetlet.2007.05.148.
- Meskens, F. A. J. Methods for the Preparation of Acetals from Alcohols or Oxiranes and Carbonyl Compounds. Synthesis 1981, 501–522. DOI: https://doi.org/10.1055/s-1981-29507.
- Aitken, R. A.; Hill, L. 1,3-Dioxoles and 1,3-Oxathioles. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon, 1996; Vol. 3, pp 525–567. DOI: https://doi.org/10.1016/B978-008096518-5.00068-X.
- Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3 ed. John Wiley & Sons, 1999; pp 293–368. DOI: https://doi.org/10.1002/0471220574.ch4.
- Sartori, G.; Ballini, R.; Bigi, F.; Bosica, G.; Maggi, R.; Righi, P. Protection (and Deprotection) of Functional Groups in Organic Synthesis by Heterogeneous Catalysis. Chem. Rev. 2004, 104, 199–250. DOI: https://doi.org/10.1021/cr0200769.
- Ram, V. J.; Sethi, A.; Nath, M.; Pratap, R. The Chemistry of Heterocycles. Nomenclature and Chemistry of Three-to-Five Membered Heterocycles. Elsevier, 2019; pp 149–478. DOI: https://doi.org/10.1016/B978-0-08-101033-4.00005-X.
- Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3 ed. John Wiley & Sons, 1999; pp 454–493. DOI: https://doi.org/10.1002/0471220574.ch6.
- Riebsomer, J. L.; Morey, G. H. The Synthesis of Hexahydropyrimidines from 1,3-Diamines and Ketones or Aldehydes. J. Org. Chem. 1950, 15, 245–248. DOI: https://doi.org/10.1021/jo01148a005.
- Ramírez, M. A.; Ortiz, G.; Levín, G.; McCormack, W.; Blanco, M. M.; Perillo, I. A.; Salerno, A. Rapid and Efficient Synthesis of Five- to Eight-Membered Cyclic Aminals under Ultrasound Irradiation. Tetrahedron Lett. 2014, 55, 4774–4776. DOI: https://doi.org/10.1016/j.tetlet.2014.06.061.
- Bagga, M. M.; Everatt, B.; Hinton, I. G. A Novel Reaction of Formaldehyde with Some Diamines. J. Chem. Soc., Chem. Commun. 1987, 259–261. DOI: https://doi.org/10.1039/c39870000259.
- Bergmann, E. D.; Kaluszyner, A. Reaction Products of Primary β-Hydroxyamines with Carbonyl Compounds. XIV. Reaction of 3-Aminopropanol with Carbonyl Compounds. Recl. Trav. Chim. Pays-Bas. 1959, 78, 315–326. DOI: https://doi.org/10.1002/recl.19590780502.
- Artemov, A. N.; Sazonova, E. V.; Krylova, N. A.; Zvereva, E. A.; Pechen, N. A.; Fukin, G. K.; Cherkasov, A. V.; Faerman, V. I.; Grishina, N. Y. The Synthesis of New 1,3-Oxazolidines and 1,3-Oxazinanes Containing (η6-Arene)Tricarbonylchromium Group Based on Condensation between Aldehydes and Amino Alcohols. Russ. Chem. Bull. 2018, 67, 884–892. DOI: https://doi.org/10.1007/s11172-018-2153-0.
- Palchykov, V. A.; Gaponov, A. A. 1,3-Amino Alcohols and Their Phenol Analogs in Heterocyclization Reactions. Adv. Heterocycl. Chem. 2020, 131, 285–350. DOI: https://doi.org/10.1016/bs.aihch.2019.06.001.
- Issleib, K.; Hannig, H.-J. 1,3-Thiaphospholane. Phosphorus 1973, 3, 113–116.
- Issleib, K.; Thorausch, P.; Reyes, W. 1,3-Thiaphospholane. Z. Chem. 1976, 16, 276–278. DOI: https://doi.org/10.1002/j.0044-2402.1976.tb00172.x.
- Issleib, K.; Hannig, H.-J. 1,3-Thiaphosphorinane. Z. Anorg. Allg. Chem. 1973, 402, 189–192. DOI: https://doi.org/10.1002/zaac.19734020209.
- Issleib, K.; Oehme, H.; Scheibe, M. 1,3-Oxaphosphorinane. Synth. Inorg. Metal-Org. Chem. 1972, 2, 223–229. DOI: https://doi.org/10.1080/00945717208069604.
- Oehme, H.; Leißtring, E. PH-Funktionelle 1,3-Oxaphosphorinane. Z. Chem. 2010, 13, 291–292. DOI: https://doi.org/10.1002/zfch.19730130807.
- Issleib, K.; Oehme, H.; Leißring, E. Perhydro-1.3-Azaphosphorine. Chem. Ber. 1968, 101, 4032–4035. DOI: https://doi.org/10.1002/cber.19681011204.
- Issleib, K.; Oehme, H.; Wienbeck, D. Zur Bildung von 3-Element-1-Phosphor-Heterocyclen. J. Organometal. Chem. 1974, 76, 345–348. DOI: https://doi.org/10.1016/S0022-328X(00)87381-7.
- Issleib, K.; Leissring, E.; Meyer, H. 1.3-Benzodiphosphole, 1.2-Bis-Dimethylaminoalkylidenphosphino-Benzen. Tetrahedron Lett. 1981, 22, 4475–4478. DOI: https://doi.org/10.1016/S0040-4039(01)93018-7.
- Issleib, K.; Leissring, E.; Schmidt, H. Reactivity of 1.2-Diphosphinobenzene. Phosphorus Sulfur Relat. Elem. 1983, 18, 15–18. DOI: https://doi.org/10.1080/03086648308075956.
- Issleib, K.; Schmidt, H.; Bergmann, P. Reaktion des Aktivierten 1,2-Diphosphinobenzens mit Diphenylcarbodiimid. Z. Anorg. Allg. Chem. 1985, 529, 216–221. DOI: https://doi.org/10.1002/zaac.19855291027.
- Issleib, K.; Schmidt, H.; Leissring, E. 1,3-Benzodiphosphole; ein Beitrag zur Chemie benzokondensierter 1,3-Elementphosphole. J. Organomet. Chem. 1990, 382, 53–60. DOI: https://doi.org/10.1016/0022-328X(90)85214-J.
- Schmidt, H.; Issleib, K.; Leissring, E. 1,3-Benzodiphospholes – Synthesis and Reactivity. Phosphorus Sulfur Silicon Relat. Elem. 1990, 49-50, 355–358. DOI: https://doi.org/10.1080/10426509008038978.
- Mathey, F. Product Class 7: Diphospholes. In Science of Synthesis, 12: Category 2, Hetarenes and Related Ring Systems; Neier, R., Bellus, D., Eds.; Thieme: Stuttgart, 2002, pp 705–718. DOI: https://doi.org/10.1055/sos-SD-012-00894.
- Issleib, K.; Oehme, H. Zur Kondensation sek.-4-Aminobutylphosphine mit Aldehyden und Ketonen. Z. Chem. 2010, 13, 139–141. DOI: https://doi.org/10.1002/zfch.19730130414.
- Oehme, H.; Leißring, E. 1,3-Oxaphosphepane. Z. Chem. 1979, 19, 57–59. DOI: https://doi.org/10.1002/zfch.19790190206.
- Dilworth, J. R.; Howe, S. D.; Hutson, A. J.; Miller, J. R.; Silver, J.; Thompson, R. M.; Harman, M.; Hursthouse, M. B. Complexes of Functionalised Phosphine Ligands. Part 1. Complexes of FeIII, CoIII, NiII and ReV with Tridentate Schiff Bases Having PNO, NNO and NNS Donor Sets. Crystal Structures of 2-(Ph2PC6H4N = CH)C6H4OH and [Co{2-(Ph2PC6H4CH = N)C6H4O}2][PF6]. J. Chem. Soc. Dalton Trans 1994, 3553–3562. DOI: https://doi.org/10.1039/DT9940003553.
- Scherhag, G.; Spicer, M. D. Preparation of a Cyclic Trimer with a Ni3P3 Core: Aggregation and Conformation Driven by Steric Demand. J. Chem. Soc. Dalton Trans. 2000, 1237–1238. DOI: https://doi.org/10.1039/b001098g.
- Doherty, S.; Knight, J. G.; Scanlan, T. H.; Elsegood, M. R. J.; Clegg, W. Iminophosphines: Synthesis, Formation of 2,3-Dihydro-1H-benzo[1,3]azaphosphol-3-ium Salts and N-(Pyridin-2-yl)-2-Diphenylphosphinoylaniline, Coordination Chemistry and Applications in Platinum Group Catalyzed Suzuki Coupling Reactions and Hydrosilylations. J. Organomet. Chem 2002, 650, 231–248. DOI: https://doi.org/10.1016/S0022-328X(02)01203-2.
- Gilbert-Wilson, R.; Chu, W.-Y.; Rauchfuss, T. B. Phosphine-Iminopyridines as Platforms for Catalytic Hydrofunctionalization of Alkenes. Inorg. Chem. 2015, 54, 5596–5603. DOI: https://doi.org/10.1021/acs.inorgchem.5b00692.
- Verhoeven, D. G. A.; Negenman, H. A.; Orsino, A. F.; Lutz, M.; Moret, M.-E. Versatile Coordination and C-C Coupling of Diphosphine-Tethered Imine Ligands with Ni(II) and Ni(0). Inorg. Chem. 2018, 57, 10846–10856. DOI: https://doi.org/10.1021/acs.inorgchem.8b01478.
- Oehme, H.; Leißring, E. Beitrag zur Reaktion Sekundärer Phosphine mit Aromatischen Aldehyden. Z. Chem. 2010, 19, 416–417. DOI: https://doi.org/10.1002/zfch.19790191108.
- Oehme, H.; Leissring, E. Zur Reaktion Primärer and Sekundärer Phosphine mit Aromatischen Aldehyden und Alkoholen. Tetrahedron 1981, 37, 753–759. DOI: https://doi.org/10.1016/S0040-4020(01)97693-8.
- Termaten, A.; Sluis, M.; Bickelhaupt, F. The Substituent Effect of the Phosphaalkenyl Group. Eur. J. Org. Chem. 2003, 2003, 2049–2055. DOI: https://doi.org/10.1002/ejoc.200200618.
- Maier, L.; Organische Phosphorverbindungen, X. Eine neue Methode zur Knüpfung von P-C-P-Bindungen (Darstellung von Di-, Tri- und Tetra-tertiären-Phosphinen). Helv. Chim. Acta. 1965, 48, 1034–1039. DOI: https://doi.org/10.1002/hlca.19650480507.
- Maier, L. Methylenediphosphine Products and Process for the Preparation Thereof. U.S. Patent 3,253,033, May 24, 1966.
- Kaska, W. C.; Maier, L. Organic Phosphorus Compounds 67. The Exchange Cleavage of Dialkylaminomethylphosphines with Aryl and Diarylphosphines. Helv. Chim. Acta. 1974, 57, 2550–2552. DOI: https://doi.org/10.1002/hlca.19740570829.
- Grobe, J.; Van, D. L.; Nientiedt, J. Reaktive E = C(p-p)π-Systeme VI. Reaktionen des Phosphaalkens F3CP = CF2 mit H-aciden Verbindungen. Z. Naturforsch. B. 1986, 41, 149–161. DOI: https://doi.org/10.1515/znb-1986-0203.
- Grobe, J.; Van, D. L.; Nientiedt, J.; Krebs, B.; Dartmann, M. Reaktive E = C(p-p)π-Systeme. XIV. Synthese und Struktur von Phosphaalkenen des Typs F3CP = C(F)NR2. Chem. Ber. 1988, 121, 655–664. DOI: https://doi.org/10.1002/cber.19881210411.
- Valyaev, D. A.; Filippov, O. A.; Lugan, N.; Lavigne, G.; Ustynyuk, N. A. Umpolung of Methylenephosphonium Ions in Their Manganese Half-Sandwich Complexes and Application to the Synthesis of Chiral Phosphorus-Containing Ligand Scaffolds. Angew. Chem. 2015, 127, 6413–6417. DOI: https://doi.org/10.1002/ange.201501256.
- Weber, L.; Uthmann, S.; Stammler, H.-G.; Neumann, B.; Schoeller, W. W.; Boese, R.; Bläser, D. Reactivity of Carbonyl-Functionalized Phosphaalkenes RC(O)P = C(NMe2)2 (R = tBu, Ph) towards Electrophiles. Eur. J. Inorg. Chem. 1999, 2369–2381. DOI: https://doi.org/10.1002/(SICI)1099-0682(199912)1999:12<2369::AID-EJIC2369>3.0.CO;2-S.
- Weber, L. Phosphaalkenes with Inverse Electron Density. Eur. J. Inorg. Chem. 2000, 2425–2441. DOI: https://doi.org/10.1002/1099-0682(200012)2000:12 < 2425::AID-EJIC2425 > 3.0.CO;2-A.
- Rosa, P.; Gouverd, C.; Bernardinelli, G.; Berclaz, T.; Geoffroy, M. Phosphaalkenes with Inverse Electron Density: Electrochemistry, Electron Paramagnetic Resonance Spectra, and Density Functional Theory Calculations of Aminophosphaalkene Derivatives. J. Phys. Chem. A. 2003, 107, 4883–4892. DOI: https://doi.org/10.1021/jp030023a.
- Issleib, K.; Schmidt, H.; Leissring, E. Unerwartetes Redoxverhalten bei Cyclisierungsversuchen an o-Phenylendiphosphinderivaten. J. Organomet. Chem. 1987, 330, 17–24. DOI: https://doi.org/10.1016/0022-328X(87)80274-7.
- Aluri, B. R.; Kindermann, M. K.; Jones, P. G.; Dix, I.; Heinicke, J. Bulky N-Substituted 1,3-Benzazaphospholes: Access via Pd-Catalyzed C-N and C-P Cross Coupling, Lithiation, and Conversion to Novel P = C-PtBu2 Hybrid Ligands. Inorg. Chem. 2008, 47, 6900–6912. DOI: https://doi.org/10.1021/ic800430f.
- Adam, M. S. S.; Kühl, O.; Kindermann, M. K.; Heinicke, J. W.; Jones, P. G. 3-Amino- and 3-Acylamido-2-Phosphonopyridines: Synthesis by Pd-Catalyzed P–C Coupling, Structure and Conversion to Pyrido[b]-Anellated P = C–N Heterocycles. Tetrahedron 2008, 64, 7960–7967. DOI: https://doi.org/10.1016/j.tet.2008.06.010.
- Ghalib, M.; Jones, P. G.; Lysenko, S.; Heinicke, J. W. Enantiomerically Pure N Chirally Substituted 1,3-Benzazaphospholes: Synthesis, Reactivity toward tBuLi, and Conversion to Functionalized Benzazaphospholes and Catalytically Useful Dihydrobenzazaphospholes. Organometallics 2014, 33, 804–816. DOI: https://doi.org/10.1021/om401184n.
- Chernega, A. N.; Ruban, A. V.; Romanenko, V. D.; Markovski, L. N.; Korkin, A. A.; Antipin, M. Y.; Struchkov, Y. T. Peculiarities of pπ-pπ Conjugation in Aminosubstituted Phosphaalkenes. Heteroat. Chem. 1991, 2, 229–241. DOI: https://doi.org/10.1002/hc.520020205.
- Müller, C.; Bartsch, R.; Fischer, A.; Jones, P. G.; Schmutzler, R. Reactions of Phosphaalkenes with Hexafluoroacetone. Chem. Ber. 1995, 128, 499–502. DOI: https://doi.org/10.1002/cber.19951280511.
- Ghalib, M.; Jones, P. G.; Heinicke, J. W. Solvent-Controlled Lithiation of P = C–N-Heterocycles: Synthesis of Mono- and Bis(Trimethylsilyl)-tert-Butyl-Dihydrobenzazaphospholes—A New Type of Highly Bulky and Basic Phosphine Ligands. J. Organomet. Chem. 2014, 763-764, 44–51. DOI: https://doi.org/10.1016/j.jorganchem.2014.04.014.
- Navech, J.; Majoral, J. P.; Meriem, A.; Kramer, R. Thermal and Photochemical Reactivity of Phosphaalkenes. Phosphorus Sulfur Silicon Relat. Elem. 1983, 18, 27–30. DOI: https://doi.org/10.1080/03086648308075959.
- Issleib, K.; Schmidt, H.; Leissring, E. Zum Cyclisierungsverhalten von 2-Aminoethylphosphinen. J. Organomet. Chem. 1988, 355, 71–77. DOI: https://doi.org/10.1016/0022-328X(88)89011-9.
- Swor, C. D. Synthesis, Coordination Chemistry, and Reactivity of Functionalized Phosphines: Toward Water-Soluble Macrocyclic Phosphine Complexes. Ph.D. Dissertation, The University of Oregon, Eugene, U.S., 2011.
- Imamoto, T.; Oshiki, T.; Onozawa, T.; Kusumoto, T.; Sato, K. Synthesis and Reactions of Phosphine-Boranes. Synthesis of New Bidentate Ligands with Homochiral Phosphine Centers via Optically Pure Phosphine-Boranes. J. Am. Chem. Soc. 1990, 112, 5244–5252. DOI: https://doi.org/10.1021/ja00169a036.
- Hayashi, M.; Ishitobi, H.; Matsuura, Y.; Matsuura, T.; Watanabe, Y. Asymmetric Synthesis of α-Chiral Hydroxyalkylphosphines by a Catalytic Enantioselective Reduction of Acylphosphines. Org. Lett. 2014, 16, 5830–5833. DOI: https://doi.org/10.1021/ol5024757.
- Hayashi, M. Development of Novel Syntheses of Organophosphorus Compounds: From a Simple P-C Bond Formation to Phosphacycles. Phosphorus Sulfur Relat. Elem. 2021, 1–11. in press. DOI: https://doi.org/10.1080/10426507.2021.2008932.
- Henderson, W.; Olsen, G. M.; Bonnington, L. S. Immobilised Phosphines Incorporating the Chiral Biopolymers Chitosan and Chitin. J. Chem. Soc., Chem. Commun. 1994, 1863–1864. DOI: https://doi.org/10.1039/c39940001863.
- Oswald, P. R.; Evans, R. A.; Henderson, W.; Daniel, R. M.; Fee, C. J. Properties of a Thermostable β-Glucosidase Immobilized Using Tris(hydroxymethyl)phosphine as a Highly Effective Coupling Agent. Enzyme Microb. Technol. 1998, 23, 14–19. DOI: https://doi.org/10.1016/S0141-0229(98)00005-2.
- Petrov, K. A.; Parshina, V. A.; Erokhina, T. S.; Petrova, G. M. Preparation of Hydroxymethyl-Bis(aminomethyl)Phosphine Oxides. U.S.S.R. Patent 375,300, Mar 23, 1973.
- Goodwin, N. J.; Henderson, W.; Nicholson, B. K.; Sarfo, J. K.; Fawcett, J.; Russell, D. R. Synthesis and Reactivity of the Ferrocene-Derived Phosphine [Fe(η-C5H5){η-C5H4CH2P(CH2OH)2}]. J. Chem. Soc., Dalton Trans. 1997, 4377–4384. DOI: https://doi.org/10.1039/a703666c.
- Mironova, Z. N.; Tsvetkov, E. N.; Nikolaev, A. V.; Kabachnik, M. I. Syntheses Based on Tetramethylolphosphonium Chloride. I. Tri(acetoxymethyl)phosphine as the Parent Substance for Preparing Alkyl-di(acetoxymethyl)-, Dialkyl(acetoxymethyl)-, and Trialkylphosphines. Zh. Obshch. Khim. 1967, 37, 2747–2752.
- Bianchi, M.; Frediani, P.; Salvini, A.; Rosi, L.; Pistolesi, L.; Piacenti, F.; Ianelli, S.; Nardelli, M. Synthesis, Characterization, and Behavior of Hydridoruthenium Carbonyl Clusters Substituted with Functionalized Phosphines in the Presence of Hydrogen. 1. H4Ru4(CO)8[P(CH2OCOR)3]4 (R = CH3-, C2H5-, (CH3)2CH-, (CH3)3C-, (S)-C2H5CH(CH3)-). Organometallics 1997, 16, 482–489. DOI: https://doi.org/10.1021/om960037l.
- Mironova, Z. N.; Tsvetkov, E. N.; Petrovskaya, L. I.; Negrebetsky, V. V.; Nikolaev, A. V.; Kabachnik, M. I. Syntheses Based on Tetramethylolphosphonium Chloride. Aminomethylphosphines and Their Oxides. Zh. Obshch. Khim. 1972, 42, 2152–2158.
- Valetdinov, R. K.; Zaripov, S. I.; Yarkova, E. G. Reaction of Alkylbis(β-hydroxyalkyl)phosphines with Dialkylamines. Zh. Obshch. Khim. 1976, 46, 275–277.
- Slany, M.; Höhn, A. Cis-verbrückte Metallkomplexe. Ger. Patent 196 51 685, Aug 20, 1998.
- Li, W.; Zhang, J. Recent Developments in the Synthesis and Utilization of Chiral β-Aminophosphine Derivatives as Catalysts or Ligands. Chem. Soc. Rev. 2016, 45, 1657–1677. DOI: https://doi.org/10.1039/C5CS00469A.
- Märkl, G.; Merkl, B. Optisch aktive β(Amino)ethyl-phosphonsäureester, β(Amino)ethyl-phenylphosphinsäureester, β(Amino)ethyl-diphenylphosphinoxide und β(Amino)ethyl-diphenylphosphine. Tetrahedron Lett. 1981, 22, 4459–4462. DOI: https://doi.org/10.1016/S0040-4039(01)93014-X.
- Kabachnik, M. I.; Tsvetkov, E. N.; Chung-Yu, C. Orientation of Addition and Reactivity of Vinyl Group in Reactions of Secondary Amines with Vinyl P(III)- and P(V)-Compounds. Zh. Obshch. Khim. 1962, 32, 3340–3350.
- Rahman, M. S.; Steed, J. W.; Hii, K. K. Scope and Limitations of the Preparation of Aminophosphines R-NH(CH2CH2PPh2) and Aminodiphosphines R-N(CH2CH2PPh2)2 via Michael Addition of Amines to Vinylphosphines. Synthesis 2000, 1320–1326. DOI: https://doi.org/10.1055/s-2000-6422.
- Paetzold, E.; Michalik, M.; Oehme, G. Synthesis of a New Type of Water-Soluble Phosphines by Addition of Hydrophilic Thiols to Vinylphosphines. Preparation of the Rhodium and Palladium Complexes. J. Prakt. Chem. 1997, 339, 38–43. DOI: https://doi.org/10.1002/prac.19973390106.
- Kabachnik, M. I.; Medved', T. Y.; Polikarpov, Y. M.; Yudina, K. S. Reactions of Diphenylvinylphosphine Oxide. Russ. Chem. Bull. 1962, 11, 1499–1503. DOI: https://doi.org/10.1007/BF00907224.
- Oliana, M.; King, F.; Horton, P. N.; Hursthouse, M. B.; Hii, K. K. Practical Synthesis of Chiral Vinylphosphine Oxides by Direct Nucleophilic Substitution. Stereodivergent Synthesis of Aminophosphine Ligands. J. Org. Chem. 2006, 71, 2472–2479. DOI: https://doi.org/10.1021/jo052575q.
- Ben-Aroya, B. B.-N.; Portnoy, M. Preparation of α-Aminophosphines on Solid Support: Model Studies and Parallel Synthesis. Tetrahedron 2002, 58, 5147–5158. DOI: https://doi.org/10.1016/S0040-4020(02)00471-4.
- Oehme, H.; Leissring, E.; Zschunke, A. Synthese und Stereochemie der 1-Amino- und 1-Phenylamino-1,3-Azaphospholan-5-One. Phosphorus Sulfur Silicon Relat. Elem. 1978, 4, 59–66. DOI: https://doi.org/10.1080/03086647808079966.
- Pap, L. G.; Arulsamy, N.; Hulley, E. B. Tridentate Phosphine Ligands Bearing Aza-Crown Ether Lariats. Polyhedron 2018, 141, 385–392. DOI: https://doi.org/10.1016/j.poly.2017.11.012.
- Andrieu, J.; Dietz, J.; Poli, R.; Richard, P. Reversible P–C Bond Formation for Saturated α-Aminophosphine Ligands in Solution: Stabilization by Coordination to Cu(I). New J. Chem. 1999, 23, 581–583. DOI: https://doi.org/10.1039/a902783a.
- Andrieu, J.; Baldoli, C.; Maiorana, S.; Poli, R.; Richard, P. Chiral α‐P,N Ligands from a Diastereoselective Ph2PH Addition to (η6‐Benzaldimine)Tricarbonylchromium Complexes. Eur. J. Org. Chem. 1999, 3095–3097. DOI: https://doi.org/10.1002/(SICI)1099-0690(199911)1999:11<3095::AID-EJOC3095>3.0.CO;2-Q.
- Camus, J.-M.; Andrieu, J.; Poli, R.; Richard, P.; Baldoli, C.; Maiorana, S. Rh(I) Coordination Chemistry of Chiral α-aminophosphine(η6-arene)Chromium Tricarbonyl Ligands. Inorg. Chem. 2003, 42, 2384–2390. DOI: https://doi.org/10.1021/ic025588k.
- Arbuzov, B. A.; Erastov, O. A.; Nikonov, G. N. Exchange of Radicals at Nitrogen Atoms in Aminomethyl Derivatives of Phenylphosphines. Izv. Akad. Nauk SSSR, Ser. Khim. 1980, 2417–2420.
- Arbuzov, B. A.; Erastov, O. A.; Nikonov, G. N.; Arshinova, R. P.; Romanova, I. P.; Kadyrov, R. A. Synthesis and Structure of 1,5-Diaza-3,7-Diphosphacyclooctanes. Russ. Chem. Bull. 1983, 32, 1672–1676. DOI: https://doi.org/10.1007/BF00954289.
- Stickel, M.; Maichle-Moessmer, C.; Wesemann, L.; Mayer, H. A. Reprint of Bis(Phosphinomethyl)Phenylamines and Bis(Phosphinomethyl)Sulfides and Their Reaction with d8-Platinum Group Precursors. Polyhedron 2013, 52, 1471–1480. DOI: https://doi.org/10.1016/j.poly.2013.02.001.
- Musina, E. I.; Wittmann, T. I.; Strelnik, I. D.; Naumova, O. E.; Karasik, A. A.; Krivolapov, D. B.; Islamov, D. R.; Kataeva, O. N.; Sinyashin, O. G.; Lönnecke, P.; et al. Influence of the rac–meso Isomerization of Seven-Membered Cyclic Bisphosphines on the Predominant Formation of Chelate Complexes. Polyhedron 2015, 100, 344–350. DOI: https://doi.org/10.1016/j.poly.2015.08.033.
- Andrieu, J.; Richard, P.; Camus, J.-M.; Poli, R. Synthesis, Coordination to Rh(I), and Hydroformylation Catalysis of New β-Aminophosphines Bearing a Dangling Nitrogen Group: An Unusual Inversion of a Rh-Coordinated P Center. Inorg. Chem. 2002, 41, 3876–3885. DOI: https://doi.org/10.1021/ic011035i.
- Durran, S. E.; Smith, M. B.; Slawin, A. M. Z.; Gelbrich, T.; Hursthouse, M. B.; Light, M. E. Synthesis and Coordination Studies of New Aminoalcohol Functionalized Tertiary Phosphines. Can. J. Chem. 2001, 79, 780–791. DOI: https://doi.org/10.1139/v01-037.
- De'Ath, P.; Elsegood, M. R. J.; Halliwell, C. A. G.; Smith, M. B. Mild Intramolecular P–C(sp3) Bond Cleavage in Bridging Diphosphine Complexes of RuII RhIII and IrIII. J. Organomet. Chem. 2021, 937, 121704. DOI: https://doi.org/10.1016/j.jorganchem.2021.121704.
- Płotek, M.; Starosta, R.; Komarnicka, U. K.; Skórska-Stania, A.; Stochel, G.; Kyzioł, A.; Jeżowska-Bojczuk, M. Unexpected Formation of [Ru(η5-C5H5)(PH{CH2N(CH2CH2)2O}2) (PPh3)2]BF4—The First “Piano-Stool” Ruthenium Complex Bearing a Secondary Aminomethylphosphane Ligand. RSC Adv. 2015, 5, 2952–2955. DOI: https://doi.org/10.1039/C4RA13037E.
- Płotek, M.; Starosta, R.; Komarnicka, U. K.; Skórska-Stania, A.; Kołoczek, P.; Dudek, K.; Kyzioł, A. Tertiary to Secondary Reduction of Aminomethylphosphane Derived from 1-Ethylpiperazine as a Result of Its Coordination to Ruthenium(II) Centre—The First Insight into the Nature of Process. J. Mol. Struct. 2016, 1121, 104–110. DOI: https://doi.org/10.1016/j.molstruc.2016.05.053.
- Higham, L.; Powell, A. K.; Whittlesey, M. K.; Wocadlo, S.; Wood, P. T. Formation and X-Ray Structure of a Novel Water-Soluble Tertiary-Secondary Phosphine Complex of Ruthenium(II): [Ru{P(CH2OH)3}2{P(CH2OH)2H}2Cl2]. Chem. Commun. 1998, 1107–1108. DOI: https://doi.org/10.1039/a801546e.
- Higham, L. J.; Whittlesey, M. K.; Wood, P. T. Water-Soluble Hydroxyalkylated Phosphines: Examples of Their Differing Behaviour toward Ruthenium and Rhodium. Dalton Trans. 2004, 4202–4208. DOI: https://doi.org/10.1039/b411701h.
- Sweetman, B. J. The Specificity of Certain Phosphine Derivatives as Reducing Agents for the Disulfide Bond in Wool Keratin. Text. Res. J. 1966, 36, 1096–1101. DOI: https://doi.org/10.1177/004051756603601210.
- Andrieu, J.; Camus, J.-M.; Poli, R.; Richard, P. New Chiral α-Aminophosphine Oxides and Sulfides: An Unprecedented Rhodium-Catalyzed Ligand Epimerization. New J. Chem. 2001, 25, 1015–1023. DOI: https://doi.org/10.1039/b100217l.
- Heinicke, J.; Lach, J.; Basvani, K. R.; Peulecke, N.; Jones, P. G.; Köckerling, M. α-Phosphino Amino Acids: Synthesis, Structure, and Reactivity. Phosphorus Sulfur Silicon Relat. Elem. 2011, 186, 666–677. DOI: https://doi.org/10.1080/10426507.2010.514485.
- Heinicke, J.; Lach, J.; Peulecke, N.; Jones, P. G.; Dix, I. Phosphinoglycines and Phosphinoglycolates. Phosphorus Sulfur Silicon Relat. Elem. 2008, 183, 783–786. DOI: https://doi.org/10.1080/10426500701808101.
- Hoefnagel, A. J.; van Bekkum, H.; Peters, J. A. The Reaction of Glyoxylic Acid with Ammonia Revisited. J. Org. Chem. 1992, 57, 3916–3921. DOI: https://doi.org/10.1021/jo00040a035.
- Ogo, S.; Uehara, K.; Abura, T.; Fukuzumi, S. pH-Dependent Chemoselective Synthesis of α-Amino Acids. Reductive Amination of α-keto Acids with Ammonia Catalyzed by Acid-Stable Iridium Hydride Complexes in Water. J. Am. Chem. Soc. 2004, 126, 3020–3021. DOI: https://doi.org/10.1021/ja031633r.
- Sim, Y. E.; Nwajiobi, O.; Mahesh, S.; Cohen, R. D.; Reibarkh, M. Y.; Raj, M. Secondary Amine Selective Petasis (SASP) Bioconjugation. Chem. Sci. 2020, 11, 53–61. DOI: https://doi.org/10.1039/C9SC04697F.
- Basvani, K. R.; Fomina, O. S.; Yakhvarov, D. G.; Heinicke, J. Synthesis and Properties of Zwitterionic Phosphonioglycolates. Polyhedron 2014, 67, 306–313. DOI: https://doi.org/10.1016/j.poly.2013.09.016.
- Musina, E. I.; Fesenko, T. I.; Strelnik, I. D.; Polyancev, F. M.; Latypov, S. K.; Lönnecke, P.; Hey-Hawkins, E.; Karasik, A. A.; Sinyashin, O. G. Synthesis and Unique Reversible Splitting of 14-Membered Cyclic Aminomethylphosphines on to 7-Membered Heterocycles. Dalton Trans. 2015, 44, 13565–13572. DOI: https://doi.org/10.1039/C5DT01910A.
- Musina, E. I.; Naumov, R. N.; Kanunnikov, K. B.; Dobrynin, A. B.; Gómez-Ruiz, S.; Lönnecke, P.; Hey-Hawkins, E.; Karasik, A. A.; Sinyashin, O. G. Chiral [16]-ane P4N2 Macrocycles: Stereoselective Synthesis and Unexpected Intermolecular Exchange of Endocyclic Fragments. Dalton Trans. 2018, 47, 16977–16984. DOI: https://doi.org/10.1039/C8DT03214A.
- Musina, E.; Wittmann, T.; Latypov, S.; Kondrashova, S.; Lönnecke, P.; Litvinov, I.; Hey‐Hawkins, E.; Karasik, A. Self-Assembly of Chiral 1,8-Diaza-3,6,10,13-Tetraphosphacyclotetradecanes via Dynamic Transformation of 7- and 14-Membered Aminomethylphosphines. Eur. J. Inorg. Chem. 2019, 3053–3060. DOI: https://doi.org/10.1002/ejic.201900386.
- Musina, E. I.; Wittmann, T. I.; Musin, L. I.; Balueva, A. S.; Shpagina, A. S.; Litvinov, I. A.; Lönnecke, P.; Hey-Hawkins, E.; Karasik, A. A.; Sinyashin, O. G. Dynamic Covalent Chemistry Approach Toward 18-Membered P4N2 Macrocycles and Their Nickel(II) Complexes. J. Org. Chem. 2020, 85, 14610–14618. DOI: https://doi.org/10.1021/acs.joc.0c01317.
- Bader, A.; Nullmeyers, T.; Pabel, M.; Salem, G.; Willis, A. C.; Wild, S. B. Stereochemistry and Stability of Free and Coordinated Secondary Phosphines. Crystal and Molecular Structure of [S-[(R*,R*),(R*)]]-(+)589-[PtCl{1,2-C6H4(PMePh)2} (PHMePh)]PF6.CH2Cl2. Inorg. Chem. 1995, 34, 384–389. DOI: https://doi.org/10.1021/ic00105a058.
- Bader, A.; Pabel, M.; Willis, A. C.; Wild, S. B. First Resolution of a Free Secondary Phosphine Chiral at Phosphorus and Stereospecific Formation and Structural Characterization of a Homochiral Secondary Phosphine-Borane Complex. Inorg. Chem. 1996, 35, 3874–3877. DOI: https://doi.org/10.1021/ic951494h.
- Huang, Y.; Pullarkat, S. A.; Teong, S.; Chew, R. J.; Li, Y.; Leung, P.-H. Palladacycle-Catalyzed Asymmetric Intermolecular Construction of Chiral Tertiary P-Heterocycles by Stepwise Addition of H–P–H Bonds to Bis(enones). Organometallics 2012, 31, 4871–4875. DOI: https://doi.org/10.1021/om300405h.
- Payet, E.; Auffrant, A.; Le Goff, X. F.; Le Floch, P. Phosphine- and Thiophosphorane-Amine Ligands: Lithiation and Coordination to Rh(I). J. Organomet. Chem. 2010, 695, 1499–1506. DOI: https://doi.org/10.1016/j.jorganchem.2010.03.006.
- Cui, P.; Huang, X.; Du, J.; Huang, Z. P-C Bond Cleavage Induced Ni(II) Complexes Bearing Rare-Earth-Metal-Based Metalloligand and Reactivities toward Isonitrile, Nitrile, and Epoxide. Inorg. Chem. 2021, 60, 3249–3258. DOI: https://doi.org/10.1021/acs.inorgchem.0c03675.
- Cui, P.; Wu, C.; Du, J.; Luo, G.; Huang, Z.; Zhou, S. Three-Coordinate Pd(0) with Rare-Earth Metalloligands: Synergetic CO Activation and Double P-C Bond Cleavage-Formation Reactions. Inorg. Chem. 2021, 60, 9688–9699. DOI: https://doi.org/10.1021/acs.inorgchem.1c00990.
- Han, H. Ligand Designs for Polynuclear and Heterometallic Complexes. Ph.D. Dissertation, University of Windsor, Windsor, Ontario, Canada, 2007.
- Basvani, K. R.; Kindermann, M. K.; Frauendorf, H.; Schulzke, C.; Jones, P. G.; Heinicke, J. W. 3-Phenylphosphaprolines – Synthesis, Structure and Properties of Heterocyclic α-Phosphanyl Amino Acids. Polyhedron 2017, 130, 195–204. DOI: https://doi.org/10.1016/j.poly.2017.04.014.
- Davies, D. L.; Healey, F. I.; Howarth, J.; Russell, D. R.; Sherry, L. J. S. Synthesis and Reactivity of Aminomethyldiphenylphosphine Complexes of Molybdenum. Crystal Structure of Cis-[Mo(CO)4 (Ph2PCH2NHC6H4Me-p)2]. J. Organomet. Chem. 1989, 376, C31–C34. DOI: https://doi.org/10.1016/0022-328X(89)85153-8.
- Daigle, D. J.; Pepperman, A. B.; Vail, S. L. Formaldehyde: The Key to Depolymerization of the THPOH-NH3 Polymer. Text. Res. J. 1975, 45, 350–351. DOI: https://doi.org/10.1177/004051757504500413.
- Pepperman, A. B.; Daigle, D. J.; Vail, S. L. Flameproofing Resins for Organic Textiles from Adduct Polymers. U.S. Patent 3,953,165, Apr 27, 1976.
- Vail, S. L.; Pepperman, A. B.; Daigle, D. J.; Reeves, W. A. An Examination of Reactions Occurring during Finishing with Hydroxymethylphosphines. J. Fire Flamm., Fire Retard. Chem. Suppl. 1975, 2, 161–170.
- Daigle, D. J.; Boudreaux, G. J.; Vail, S. L. Phosphaadamantanes: Reaction with Formaldehyde in Acid Solution. J. Chem. Eng. Data. 1976, 21, 240–241. DOI: https://doi.org/10.1021/je60069a032.
- Albright & Wilson Ltd. Substituted Organic Phosphine Derivatives. Br. Patent 854,182, Nov 16, 1960.
- Grekov, L. I.; Novakov, I. A. Kinetics of Phosphine Hydroxymethylation with Formaldehyde. Kinet. Catal. 2006, 47, 358–366. DOI: https://doi.org/10.1134/S0023158406030062.
- Höhn, A.; Geue, R. J.; Sargeson, A. M.; Willis, A. C. Phospha-Capped Cobalt(III) Cage Molecules: Synthesis, Properties, and Structure. J. Chem. Soc., Chem. Commun. 1989, 1644–1645. DOI: https://doi.org/10.1039/C39890001644.
- Coates, H.; Lawless, J. J. Improvements in or Relating to the Manufacture of Substituted Organic Phosphine Derivatives. Br. Patent 919,267, Feb 20, 1963.
- Prishchenko, A. A.; Livanstov, M. V.; Zhutskii, P. V.; Petrosyan, V. S. Method of Producing Tris(dialkylaminomethyl)phosphines. U.S.S.R. Patent 1,618,747, Jan 7, 1991.
- Prishchenko, A. A.; Livanstov, M. V.; Zhutskii, P. V.; Petrosyan, V. S. α-Heteroakylation of Tris(Trimethylsilyl)Phosphine. Zh. Obshch. Khim. 1990, 60, 460–461.
- Prishchenko, A. A.; Livantsov, M. V.; Novikova, O. P.; Livantsova, L. I.; Petrosyan, V. S. 1-Heteroakylation of Tris(Trimethylsilyl)Phosphine. Heteroatom Chem. 2010, 21, 441–445. DOI: https://doi.org/10.1002/hc.20636.
- Prishchenko, A. A.; Livanstov, M. V.; Pisarnitskii, D. A.; Petrosyan, V. S. Interactions of Tris(trimethylsilyl)phosphine with Chloromethylamines (Amides). Zh. Obshch. Khim. 1991, 61, 1016–1017.
- Doddi, A.; Bockfeld, D.; Bannenberg, T.; Jones, P. G.; Tamm, M. N-Heterocyclic Carbene-Phosphinidyne Transition Metal Complexes. Angew. Chem. Int. Ed. 2014, 53, 13568–13572. DOI: https://doi.org/10.1002/anie.201408354.
- Bhattacharjee, J.; Peters, M.; Bockfeld, D.; Tamm, M. Isoselective Polymerization of rac-Lactide by Aluminum Complexes of N-Heterocyclic Carbene-Phosphinidene Adducts. Chemistry 2021, 27, 5913–5918. DOI: https://doi.org/10.1002/chem.202100482.
- Bispinghoff, M.; Tondreau, A. M.; Grützmacher, H.; Faradji, C. A.; Pringle, P. G. Carbene Insertion into a P-H Bond: Parent Phosphinidene-Carbene Adducts from PH3 and Bis(phosphinidene)Mercury Complexes. Dalton Trans. 2016, 45, 5999–6003. doi: https://doi.org/10.1039/C5DT01741F.
- Issleib, K.; Kühne, U.; Krech, F. 6-Methyl-1.5-Aza-Phospha-Bicyclo[3.2.1]Octane. Phosphorus Sulfur Relat. Elem. 1983, 17, 73–79. DOI: https://doi.org/10.1080/03086648308077526.
- Kischkel, H.; Röschenthaler, G.-V. Reaktionen von Phosphanen MenPH3-n (n = 0–3) Mit Hexafluorisopropylidenimin. Z. Naturforsch. B. 1984, 39, 356–358. DOI: https://doi.org/10.1515/znb-1984-0314.
- Middleton, W. J.; Krespan, C. G. Fluorimines. J. Org. Chem. 1965, 30, 1398–1402. DOI: https://doi.org/10.1021/jo01016a012.
- Scott, D. J.; Cammarata, J.; Schimpf, M.; Wolf, R. Synthesis of Monophosphines Directly from White Phosphorus. Nat. Chem. 2021, 13, 458–464. DOI: https://doi.org/10.1038/s41557-021-00657-7.
- Maier, L. α‐Aminoalkylation of White Phosphorus. Angew. Chem. Int. Ed. 1965, 4, 527–527. DOI: https://doi.org/10.1002/anie.196505272.
- Maier, L. Organische Phosphorverbindungen XXVIII. Die α-Aminoalkylierung von Elementarem Weissem Phosphor. Eine Einfache Methode zur Darstellung von Tertiären Phosphinoxiden, Phosphinsäuren und Phosphonsäuren. Helv. Chim. Acta. 1967, 50, 1723–1741. DOI: https://doi.org/10.1002/hlca.19670500704.
- Maier, L. Organische Phorsphorverbindungen, XXXV. Die α-Aminoalkylierung von Elementarem Weissem Phosphor und von Biphosphinen. Darstellung und Reaktionen von Dialkylaminomethyl-Substituierten Tertiären Phosphinoxiden [1]. Helv. Chim. Acta. 1968, 51, 1608–1616. DOI: https://doi.org/10.1002/hlca.19680510716.
- Maier, L. Verfahren zur Herstellung von phosphorhaltigen Mannich-Basen. Ger. Patent 1,292,654, Apr 17, 1969.
- Maier, L. Phosphorus-Containing Mannich Bases. Br. Patent 1,120,374, Jul 17, 1968.
- Maier, L. Process for Preparing Phosphorus-Containing Mannich Bases. U.S. Patent 3,359,266, Dec 19, 1967.
- Moiseev, D. V.; James, B. R. Air-Stability of Aqueous Solutions of (HOCH2)3P and (HOCH2CH2CH2)3P. Inorg. Chim. Acta. 2011, 379, 23–27. DOI: https://doi.org/10.1016/j.ica.2011.09.043.
- Daigle, D. J.; Frank, A. W.; Kullman, R. M. H. Finishing with Ureidophosphorus: A Compound, not a Condensate. J. Fire Retard. Chem. 1979, 6, 276–284.
- Frank, A. W. Quaternary Ureidomethyl Phosphonium Salts. U.S. Patent 4,228,100, Oct 14, 1980.
- Kirk, A. S. Reactions of Novel Self-Assembled Iron(II) Phosphine Complexes. Ph.D. Dissertation, University of Bath, UK, 2008.
- Schenk, C. Etude sur la Réactivité du THP (Tris(Hydroxyméthyl) Phosphine) et Développement de Composés Potentiellement Efficaces en tant que Retardants de Flamme. Ph.D. Dissertation, Université de Neuchâtel, Neuchâtel, Switzerland, 2014.
- Frank, A. W.; Drake, G. L. Synthesis and Properties of Carbamate Derivatives of Tetrakis(Hydroxymethyl)Phosphonium Chloride. J. Org. Chem. 1977, 42, 4040–4045. DOI: https://doi.org/10.1021/jo00445a010.
- Frank, A. W. Synthesis and Properties of Condensed Ureidomethyl Phosphonium Salts. Phosphorus Sulfur Relat. Elem. 1981, 10, 147–152. DOI: https://doi.org/10.1080/03086648108077497.
- Frank, A. W. Condensation of Tetrakis(Hydroxymethyl)Phosphonium Sulfates and Sulfonates with 1,3-Dimethylurea. Phosphorus Sulfur Relat. Elem. 1981, 10, 207–212. DOI: https://doi.org/10.1080/03086648108077507.
- Frank, A. W. Synthesis and Properties of Tetrakis(Ureidomethyl)Phosphonium Salts. Phosphorus Sulfur Relat. Elem. 1978, 5, 19–25. DOI: https://doi.org/10.1080/03086647808069857.
- Frank, A. W.; Daigle, D. J.; Kullman, R. M. H. Ternary Salts of Tris(aminomethyl)phosphines and Their Oxides. U.S. Patent 4,196,149, Apr 1, 1980.
- Nachbur, H.; Maeder, A. Verfahren zur Herstellung von phosphorhaltigen Kondensationsprodukten, die Produkte und ihre Verwendung als Flammschutzmittel. Ger. Patent 2,242,690, Mar 15, 1973.
- Stricklen, P. M. Phosphorus-31 NMR of Some Bicyclic Phosphorus Compounds. Ph.D. Dissertation, Iowa State University, Ames, Iowa, 1979.
- Coates, H.; Hoye, P. A. T. Substituted Organic Phosphine Derivatives. Br. Patent 842,593, Jul 27, 1960.
- Petrov, K. A.; Parshina, V. A.; Orlov, B. A.; Tsypina, G. M. Properties of Phosphines. V. Reactions of Phosphines with Chloramines, Sulfenyl Chlorides, and Amines. Zh. Obshch. Khim. 1962, 32, 4017–4022.
- Krauter, J. G. E.; Beller, M. An Easy and Practical Synthetic Route to Electron Rich Water Soluble Ligands: α-Aminomethylation of Trishydroxymethylphosphine. Tetrahedron 2000, 56, 771–774. DOI: https://doi.org/10.1016/S0040-4020(99)01056-X.
- Starosta, R.; Komarnicka, U. K.; Puchalska, M. Solid State Luminescence of CuI and CuNCS Complexes with Phenanthrolines and a New Tris(Aminomethyl)Phosphine Derived from N-Methyl-2-Phenylethanamine. J. Lumin. 2014, 145, 430–437. DOI: https://doi.org/10.1016/j.jlumin.2013.07.015.
- Schapira, J.; Mai-Xuan, K.; Askienazy, A. Dérivés du Phosphore, Leur Procédé de Préparation et Leurs Applications. Fr. Patent 2,157,108, Jun 1, 1973.
- Carlson, R. H. Metal Sequestrant. U.S. Patent 3,578,708, May 11, 1971.
- Carlson, R. H. Synergistic Metal Sequestrant. U.S. Patent 3,661,960, May 9, 1972.
- Märkl, G.; Jin, G. Y.; Schoerner, C. Chirale Aminomethyl-Phosphine und Aminomethyl-Diphosphine. Tetrahedron Lett. 1980, 21, 1845–1848. DOI: https://doi.org/10.1016/S0040-4039(00)92795-3.
- Daigle, D. J.; Reeves, W. A.; Donaldson, D. J. Reaction of THPOH with Secondary Amines. Text. Res. J. 1970, 40, 580–581. DOI: https://doi.org/10.1177/004051757004000612.
- Reeves, W. A.; Daigle, D. J.; Donaldson, D. J.; Drake, G. L. Methylol Phosphorus Polymers Used for Flame Retardants. Text. Chem. Color. 1970, 2, 283–285.
- Daigle, D. J.; Pepperman, A. B.; Reeves, W. A. The Role of Formaldehyde in the Production of Tris(Diphenylaminomethyl)Phosphine. Text. Res. J. 1971, 41, 944–945. DOI: https://doi.org/10.1177/004051757104101114.
- Mironova, Z. N.; Tsvetkov, E. N.; Nikolaev, A. V.; Kabachnik, M. I. Aminomethylphosphines. U.S.S.R. Patent 247,296, Jul 4, 1969.
- Stewart, M. J.; Price, J. A. Stabilization of Saturated Linear Polyesters with Phosphines. U.S. Patent 3,496,137, Feb 17, 1970.
- Oftedahl, E. N. Phosphine Sensitized Photographic Silver Halide Emulsions and Elements. U.S. Patent 3,904,415, Sep 9, 1975.
- Starosta, R.; Florek, M.; Król, J.; Puchalska, M.; Kochel, A. Copper(I) Iodide Complexes Containing New Aliphatic Aminophosphine Ligands and Diimines—Luminescent Properties and Antibacterial Activity. New J. Chem. 2010, 34, 1441–1449. DOI: https://doi.org/10.1039/b9nj00636b.
- Starosta, R.; Komarnicka, U. K.; Puchalska, M.; Barys, M. Solid State Luminescence of Copper(I) (Pseudo)Halide Complexes with Neocuproine and Aminomethylphosphanes Derived from Morpholine and Thiomorpholine. New J. Chem. 2012, 36, 1673–1683. DOI: https://doi.org/10.1039/c2nj40229g.
- Starosta, R.; Komarnicka, U. K.; Puchalska, M. Luminescent Copper(I) (Pseudo)Halide Complexes with Neocuproine and a Novel Bulky Tris(Aminomethyl)Phosphine Derived from 2-Piperazinopyridine. J. Lumin. 2013, 143, 137–144. DOI: https://doi.org/10.1016/j.jlumin.2013.04.050.
- Starosta, R.; Bazanów, B.; Barszczewski, W. Chalcogenides of the Aminomethylphosphines Derived from 1-Methylpiperazine, 1-Ethylpiperazine and Morpholine: NMR, DFT and Structural Studies for Determination of Electronic and Steric Properties of the Phosphines. Dalton Trans. 2010, 39, 7547–7555. DOI: https://doi.org/10.1039/c0dt00037j.
- Starosta, R.; Brzuszkiewicz, A.; Bykowska, A.; Komarnicka, U. K.; Bażanów, B.; Florek, M.; Gadzała, Ł.; Jackulak, N.; Król, J.; Marycz, K. A Novel Copper(I) Complex, [CuI(2,2′-Biquinoline)P(CH2N(CH2CH2)2O)3]—Synthesis, Characterisation and Comparative Studies on Biological Activity. Polyhedron. 2013, 50, 481–489. DOI: https://doi.org/10.1016/j.poly.2012.11.033.
- Starosta, R.; Stokowa, K.; Florek, M.; Król, J.; Chwiłkowska, A.; Kulbacka, J.; Saczko, J.; Skała, J.; Jeżowska-Bojczuk, M. Biological Activity and Structure Dependent Properties of Cuprous Iodide Complexes with Phenanthrolines and Water Soluble Tris(Aminomethyl)Phosphanes. J. Inorg. Biochem. 2011, 105, 1102–1108. DOI: https://doi.org/10.1016/j.jinorgbio.2011.05.007.
- Płotek, M.; Starosta, R.; Komarnicka, U. K.; Skórska-Stania, A.; Kołoczek, P.; Kyzioł, A. Ruthenium(II) Piano Stool Coordination Compounds with Aminomethylphosphanes: Synthesis, Characterisation and Preliminary Biological Study in Vitro. J. Inorg. Biochem. 2017, 170, 178–187. DOI: https://doi.org/10.1016/j.jinorgbio.2017.02.017.
- Płotek, M.; Starosta, R.; Komarnicka, U. K.; Skórska-Stania, A.; Jeżowska-Bojczuk, M.; Stochel, G.; Kyzioł, A. New Ruthenium(II) Coordination Compounds Possessing Bidentate Aminomethylphosphane Ligands: Synthesis, Characterization and Preliminary Biological Study in Vitro. Dalton Trans. 2015, 44, 13969–13978. DOI: https://doi.org/10.1039/C5DT01119A.
- Baskakov, D.; Herrmann, W. A. Water-Soluble Metal Complexes and Catalysts: Part XI. Novel Ligands from Tris(Hydroxymethyl)Phosphane and Amino Acids: Synthesis and Catalytic Studies in Two-Phase Hydroformylation. J. Mol. Catal. A: Chem. 2008, 283, 166–170. DOI: https://doi.org/10.1016/j.molcata.2007.12.006.
- Sivriev, H.; Kaleva, V.; Borissov, G. Synthesis of Polyurethanes from Phosphorus- and Nitrogen-Containing Diols Obtained on the Basis of Tetrakis(Hydroxymethyl)Phosphonium Chloride. Eur. Polym. J. 1986, 22, 761–765. DOI: https://doi.org/10.1016/0014-3057(86)90126-6.
- Sivriev, C.; Żabski, L. Flame Retarded Rigid Polyurethane Foams by Chemical Modification with Phosphorus- and Nitrogen-Containing Polyols. Eur. Polym. J. 1994, 30, 509–514. DOI: https://doi.org/10.1016/0014-3057(94)90053-1.
- Kasem, M. A.; Richards, H. R.; Walker, C. C. Preparation and Characterization of Phosphorus-Nitrogen Polymers for Flameproofing Cellulose. I. Polymers of THPC and Amines. J. Appl. Polym. Sci. 1971, 15, 2237–2243. DOI: https://doi.org/10.1002/app.1971.070150915.
- Ma, C.; Qiu, S.; Yu, B.; Wang, J.; Wang, C.; Zeng, W.; Hu, Y. Economical and Environment-Friendly Synthesis of a Novel Hyperbranched Ploy(Aminomethylphosphine Oxide-Amine) as Co-Curing Agent for Simultaneous Improvement of Fire Safety, Glass Transition Temperature and Toughness of Epoxy Resins. Chem. Eng. J. 2017, 322, 618–631. DOI: https://doi.org/10.1016/j.cej.2017.04.070.
- Britvin, S. N.; Lotnyk, A. Water-Soluble Phosphine Capable of Dissolving Elemental Gold: The Missing Link between 1,3,5-Triaza-7-phosphaadamantane (PTA) and Verkade's Ephemeral Ligand. J. Am. Chem. Soc. 2015, 137, 5526–5535. DOI: https://doi.org/10.1021/jacs.5b01851.
- Guerriero, A.; Oberhauser, W.; Riedel, T.; Peruzzini, M.; Dyson, P. J.; Gonsalvi, L. New Class of Half-Sandwich Ruthenium(II) Arene Complexes Bearing the Water-Soluble CAP Ligand as an in Vitro Anticancer Agent. Inorg. Chem. 2017, 56, 5514–5518. DOI: https://doi.org/10.1021/acs.inorgchem.7b00915.
- Guerriero, A.; Gonsalvi, L. From Traditional PTA to Novel CAP: A Comparison between Two Adamantane Cage-Type Aminophosphines. Inorg. Chim. Acta. 2021, 518, 120251. DOI: https://doi.org/10.1016/j.ica.2021.120251.
- Reeves, W. A.; Guthrie, J. D. Ethylenimine Methylol Phosphorus Polymers. Br. Patent 764,313, Dec 28, 1956.
- Katti, K. V.; Berning, D. E.; Volkert, W. A.; Ketring, A. R.; Churchill, R. Conjugate and Method for Forming Aminomethyl Phosphorus Conjugates. U.S. Patent 5,948,386, Sep 7, 1999.
- Dimroth, K.; Grief, N.; Klapproth, A. Phosphamethincyanin-Farbstoffe mit Benzimidazolylsubstituenten. Justus Liebigs Ann. Chem. 1975, 373–386. DOI: https://doi.org/10.1002/jlac.197519750221.
- Sivriev, H.; Borissov, G.; Zabski, L.; Walczyk, W.; Jedlinski, Z. Synthesis and Studies of Phosphorus‐Containing Polyurethane Foams Based on Tetrakis(Hydroxymethyl)Phosphonium Chloride Derivatives. J. Appl. Polym. Sci. 1982, 27, 4137–4147. DOI: https://doi.org/10.1002/app.1982.070271105.
- Sivriev, H.; Kaleva, V.; Borissov, G.; Zabski, L.; Jedlinski, Z. Rigid Polyurethane Foams with Reduced Flammability, Modified with Phosphorus- and Nitrogen-Containing Polyol, Obtained from Tetrakis(Hydroxymethyl)Phosphonium Chloride. Eur. Polym. J. 1988, 24, 365–370. DOI: https://doi.org/10.1016/0014-3057(88)90200-5.
- Picklesimer, L. G. THPO Tanned Leather. U.S. Patent 2,993,744, Jul 25, 1961.
- Reeves, W. A.; Donaldson, D. J.; Daigle, D. J.; Drake, G. L.; Beninate, J. V. Process of Treating Fibrous Materials with the Reaction Product of Methylolphosphine Adducts and Nitrogenous Compounds. U.S. Patent 3,844,824, Oct 29, 1974.
- LeBlanc, D. A.; LeBlanc, R. B. Method of Applying Phosphoramide-Hydroxymethyl Phosphine Condensation Products for Textile Fire Retardation. U.S. Patent 4,020,262, Apr 26, 1977.
- LeBlanc, R. B.; Dicarlo, J. P.; LeBlanc, D. A. A New Phosphonium-Phosphoramide Condensation Product for Polyester/Cotton FR Finishing. Text. Chem. Color. 1978, 10, 75–77.
- Rublev, V. V.; Tuzhikov, O. I.; Zolotareva, V. V. Study of Ion-Exchange Properties of Methylolphosphine-Based Compounds. Zh. Prikl. Khim. 1975, 48, 2632–2636.
- Laslau, C.; Henderson, W.; Zujovic, Z. D.; Travas-Sejdic, J. Phosphine-Functionalized Polyaniline Nanostructures. Synth. Met. 2010, 160, 1173–1178. DOI: https://doi.org/10.1016/j.synthmet.2010.03.004.
- Reeves, W. A.; McMillan, O. J.; Guthrie, J. D. Chemical and Physical Properties of Aminized Cotton. Text. Res. J. 1953, 23, 527–532. DOI: https://doi.org/10.1177/004051755302300803.
- Reeves, W. A.; Drake, G. L.; McMillan, O. J.; Guthrie, J. D. Insolubility in Cuprammonium Hydroxide as a Means of Detecting Crosslinking in Chemically Modified Cotton. Text. Res. J. 1955, 25, 41–46. DOI: https://doi.org/10.1177/004051755502500106.
- Zhao, B.; Kolibaba, T. J.; Lazar, S.; Grunlan, J. C. Environmentally-Benign, Water-Based Covalent Polymer Network for Flame Retardant Cotton. Cellulose 2021, 28, 5855–5866. DOI: https://doi.org/10.1007/s10570-021-03874-y.
- Tattersall, F. Organic Phosphorus Compounds for Textiles. Rubber Plastics Age 1956, 37, 98–103.
- LeBlanc, R. B.; Badger, J. H. Aminoalkylphosphonic Acid Ester-Based Textile Fire Retardants. U.S. Patent 4,013,813, Mar 22, 1977.
- Van Zutphen, S.; Mezailles, N.; Le Floch, P. Metal-Polymer Coordination Complex Incorporating Phosphorus Atoms and Applications Using such a Complex. U.S. Patent 2010/0068143, Mar 18, 2010.
- Ellzey, S. E.; Connick, W. J.; Reeves, W. A.; Drake, G. L. Composition for Rendering Cellulosic Fabrics Water- and Oil-Repellent. U.S. Patent 3,655,413, Apr 11, 1972.
- Connick, W. J.; Ellzey, S. E. Polyfluorinated Amine Oil-Repellent, Stain-Release Fabric Treatment. U.S. Patent 3,976,818, Aug 24, 1976.
- Chance, L. H.; Drake, G. L.; Reeves, W. A. Process for Flameproofing Cellulosic Material U.S. Patent 3,403,044, Sep 24, 1968.
- Mattox, M.; Valente, E. Method and Composition to Decrease Iron Sulfide Deposits in Pipe Lines. U.S. Patent 2003/0062316, Apr 3, 2003.
- Yin, B.; Tinetti, S. M. Biocidal Compositions and Methods of Use. World Patent 2013/039769, Mar 21, 2013.
- Sun, Y.; Wang, L. Preparation Method of Modified Organic Phosphorus Tanning Agent. Chin. Patent 109593896, Apr 9, 2019.
- Liu, R.; Zhao, J.; Huang, Z.; Zhang, L.; Zou, M.; Shi, B.; Zhao, S. Nitrogen and Phosphorus Co-Doped Graphene Quantum Dots as a Nano-Sensor for Highly Sensitive and Selective Imaging Detection of Nitrite in Live Cell. Sens. Actuators B: Chem. 2017, 240, 604–612. DOI: https://doi.org/10.1016/j.snb.2016.09.008.
- Li, K.; Ji, M.; Chen, R.; Jiang, Q.; Xia, J.; Li, H. Construction of Nitrogen and Phosphorus Co-Doped Graphene Quantum Dots/Bi5O7I Composites for Accelerated Charge Separation and Enhanced Photocatalytic Degradation Performance. Chin. J. Catal. 2020, 41, 1230–1239. DOI: https://doi.org/10.1016/S1872-2067(20)63531-8.
- Luz, I.; Soukri, M.; Lail, M. Flying MOFs: Polyamine-Containing Fluidized MOF/SiO2 Hybrid Materials for CO2 Capture from Post-Combustion Flue Gas. Chem. Sci. 2018, 9, 4589–4599. DOI: https://doi.org/10.1039/C7SC05372J.
- Naasani, I. Functionalized Fluorescent Nanocrystals, and Methods for Their Preparation and Use. U.S. Patent 2006/0216759, Sep 28, 2006.
- Tulsky, E.; Huang, W.; Goodwin, J.; Zhao, W. Compositions and Methods for Functionalizing or Crosslinking Ligands on Nanoparticle Surfaces. World Patent 2010/040074, Apr 8, 2010.
- Sessarego, S.; Rodrigues, S. C. G.; Xiao, Y.; Lu, Q.; Hill, J. M. Phosphonium-Enhanced Chitosan for Cr(VI) Adsorption in Wastewater Treatment. Carbohydr. Polym. 2019, 211, 249–256. DOI: https://doi.org/10.1016/j.carbpol.2019.02.003.
- Hill, J. M.; Sessarego, S. Phosphonium-Crosslinked Chitosan and Methods for Using and Producing the Same. U.S. Patent 2019/0185588, Jun 20, 2019.
- Akech, S. R. O.; Harrison, O.; Saha, A. Removal of a Potentially Hazardous Chemical, Tetrakis (Hydroxymethyl) Phosphonium Chloride from Water Using Biochar as a Medium of Adsorption. Environ. Technol. Innov. 2018, 12, 196–210. DOI: https://doi.org/10.1016/j.eti.2018.09.002.
- Martínez-Martínez, M.; Rodríguez-Berna, G.; Bermejo, M.; Gonzalez-Alvarez, I.; Gonzalez-Alvarez, M.; Merino, V. Covalently Crosslinked Organophosphorous Derivatives-Chitosan Hydrogel as a Drug Delivery System for Oral Administration of Camptothecin. Eur. J. Pharm. Biopharm. 2019, 136, 174–183. DOI: https://doi.org/10.1016/j.ejpb.2019.01.009.
- Martínez-Moreno, J.; Mir-Palomo, S.; Merino, V.; Nácher, A.; Merino-Sanjuán, M. Development of Antibiotic Loaded Biodegradable Matrices to Prevent Superficial Infections Associated to Total Knee Arthroplasty. Colloids Surf. B 2019, 181, 1–5. DOI: https://doi.org/10.1016/j.colsurfb.2019.05.024.
- Ohshio, M.; Ishihara, K.; Maruyama, A.; Shimada, N.; Yusa, S. Synthesis and Properties of Upper Critical Solution Temperature Responsive Nanogels. Langmuir 2019, 35, 7261–7267. DOI: https://doi.org/10.1021/acs.langmuir.9b00849.
- Abdilla, A.; Shi, S.; Burke, N. A. D.; Stöver, H. D. H. Multistimuli Responsive Ternary Polyampholytes: Formation and Crosslinking of Coacervates. J. Polym. Sci. A 2016, 54, 2109–2118. DOI: https://doi.org/10.1002/pola.28078.
- Ros, S.; Burke, N. A. D.; Stöver, H. D. H. Synthesis and Properties of Charge-Shifting Polycations: Poly[3-Aminopropylmethacrylamide-co-2-(Dimethylamino)Ethyl Acrylate]. Macromolecules 2015, 48, 8958–8970. DOI: https://doi.org/10.1021/acs.macromol.5b02191.
- Hastings, D. E.; Stöver, H. D. H. Crosslinked Hydrogel Capsules for Cell Encapsulation Formed Using Amino/Betaine Dual-Functional Semibatch Copolymers. ACS Appl. Polym. Mater. 2019, 1, 2055–2067. DOI: https://doi.org/10.1021/acsapm.9b00124.
- Huang, Z. H.; McDonald, W. F.; Wright, S. C.; Taylor, A. C. Crosslinked Polyamide. U.S. Patent 6,399,714, Jun 4, 2002.
- Huang, Z. H.; McDonald, W. F.; Wright, S. C.; Taylor, A. C. Antithrombogenic Polymer Coatings. U.S. Patent 2002/0068183, Jun 6, 2002.
- Henderson, W.; Petach, H. H.; Bonnington, L. S. Poly(Phosphine Oxides) as Supports for Enzyme Immobilisation. Eur. Polym. J. 1995, 31, 981–985. DOI: https://doi.org/10.1016/0014-3057(95)00054-2.
- Sarfo, K.; Petach, H. H.; Henderson, W. Polymeric Phosphine Oxide Polyether-Derived Copolymer as a Support for Urease Immobilization. Enzyme Microb. Technol. 1995, 17, 804–808. DOI: https://doi.org/10.1016/0141-0229(94)00092-6.
- Muşină, A.; Bocokić, V.; Lavric, V.; van Zutphen, S. Phosphorus-Based Polymers for Selective Capture of Platinum Group Metals. Ind. Eng. Chem. Res. 2014, 53, 13362–13369. DOI: https://doi.org/10.1021/ie502153f.
- Musina, A.; van Zutphen, S.; Lavric, V. Late Transition Metal Recovery from a Silver Nitrate Electrolyte Using a Phosphine-Oxide Bearing Scavenger. New J. Chem. 2018, 42, 7969–7975. DOI: https://doi.org/10.1039/C7NJ04928E.
- Abdulbur-Alfakhoury, E.; van Zutphen, S.; Leermakers, M. Development of the Diffusive Gradients in Thin Films Technique (DGT) for Platinum (Pt), Palladium (Pd), and Rhodium (Rh) in Natural Waters. Talanta 2019, 203, 34–48. DOI: https://doi.org/10.1016/j.talanta.2019.05.038.
- Simonescu, C. M.; Lavric, V.; Musina, A.; Antonescu, O. M.; Culita, D. C.; Marinescu, V.; Tardei, C.; Oprea, O.; Pandele, A. M. Experimental and Modeling of Cadmium Ions Removal by Chelating Resins. J. Mol. Liq. 2020, 307, 112973. DOI: https://doi.org/10.1016/j.molliq.2020.112973.
- Abdulbur-Alfakhory, E. Development of the Diffusive Gradient in Thin-Films (DGT) Passive Sampling Technique for Platinum Group Elements (PGEs) and Its Application in Urban Rivers. Ph.D. Dissertation, the Vrije Universiteit Brussel, Brussel, Belgium, 2021.
- Sammes, N. M.; Henderson, W. Synthesis and Characterisation of a Polymeric Phosphine Containing Ancillary Ether and Amino Groups. Makromol. Chem. Rapid Commun. 1993, 14, 741–746. DOI: https://doi.org/10.1002/marc.1993.030141202.
- Thirupathi, N.; Stricklen, P. M.; Liu, X.; Oshel, R.; Guzei, I.; Ellern, A.; Verkade, J. G. Comparisons of Phosphorus Ligation Properties in P(CH2NR)3P. Inorg. Chem. 2007, 46, 9351–9363. DOI: https://doi.org/10.1021/ic0703070.
- Ekubo, A. T.; Elsegood, M. R. J.; Lake, A. J.; Smith, M. B. Intramolecular Hydrogen-Bonded Tertiary Phosphines as 1,3,5-Triaza-7-Phosphaadamantane (PTA) Analogues. Inorg. Chem. 2009, 48, 2633–2638. DOI: https://doi.org/10.1021/ic801709z.
- Ekubo, A. T.; Elsegood, M. R. J.; Smith, M. B. New Monocationic Trialkylphosphine Tetraphenylborate Salts. Phosphorus Sulfur Silicon Relat. Elem. 2011, 186, 826–829. DOI: https://doi.org/10.1080/10426507.2010.533394.
- Li, B.; Li, H.; Hu, C.-W.; Jiang, J. Structural Insights into the Substrate Binding Adaptability and Specificity of Human O-GlcNAcase. Nat. Commun. 2017, 8, 666. DOI: https://doi.org/10.1038/s41467-017-00865-1.
- Chen, C.-Y.; Padmabandu, G. Nucleotides and Primers with Removable Blocking Groups. U.S. Patent 2014/0065675, Mar 6, 2014.
- Berning, D. E.; Katti, K. V.; Barnes, C. L.; Volkert, W. A. Chemical and Biomedical Motifs of the Reactions of Hydroxymethylphosphines with Amines, Amino Acids, and Model Peptides. J. Am. Chem. Soc. 1999, 121, 1658–1664. DOI: https://doi.org/10.1021/ja9827604.
- Katti, K. V.; Kannan, R.; Katti, K. K.; Pillarsetty, N.; Barnes, C. L. New Phosphorus Chemistry Leads to Unnatural Aminoacid Trimers. Phosphorus Sulfur Silicon Relat. Elem. 2002, 177, 1587–1589. DOI: https://doi.org/10.1080/10426500212214.
- Raghuraman, K.; Katti, K. K.; Barbour, L. J.; Pillarsetty, N.; Barnes, C. L.; Katti, K. V. Characterization of Supramolecular (H2O)18 Water Morphology and Water-Methanol (H2O)15(CH3OH)3 Clusters in a Novel Phosphorus Functionalized Trimeric Amino Acid Host. J. Am. Chem. Soc. 2003, 125, 6955–6961. DOI: https://doi.org/10.1021/ja034682c.
- Katti, K. K.; Kannan, R.; Casteel, S. W.; Katti, K. V. Compounds for Treatment of Copper Overload. World Patent 03/072053, Sep 4, 2003.
- Smoleński, P.; Pruchnik, F. Aminoalkylphosphines, the Water-Soluble Chiral Phosphines. Polish J. Chem. 2007, 81, 1771–1776.
- Carlson, R. H. Synergistic Metal Sequestrant U.S. Patent 3,734,861, May 22, 1973.
- Addison, S. J. The Functionalisation of Wool by Tris(Hydroxymethyl)Phosphine for Metal Ion Recovery. M.S. Dissertation, the University of Waikato, 2009.
- Chung, C.; Lampe, K. J.; Heilshorn, S. C. Tetrakis(Hydroxymethyl)Phosphonium Chloride as a Covalent Cross-linking Agent for Cell Encapsulation Within Protein-based Hydrogels. Biomacromolecules 2012, 13, 3912–3916. DOI: https://doi.org/10.1021/bm3015279.
- Jaszczak, M.; Kolesińska, B.; Wach, R.; Maras, P.; Dudek, M.; Kozicki, M. Examination of THPC as an Oxygen Scavenger Impacting VIC Dosimeter Thermal Stability and Comparison of NVP-Containing Polymer Gel Dosimeters. Phys. Med. Biol. 2019, 64, 035019. DOI: https://doi.org/10.1088/1361-6560/aafa86.
- Jenkins, A. D.; Wolfram, L. J. The Chemistry of the Reaction between Tetrakis(Hydroxymethyl)Phosphonium Chloride and Keratin. J. Soc. Dyers Colour. 1963, 79, 55–60. DOI: https://doi.org/10.1111/j.1478-4408.1963.tb02536.x.
- Graham, J. S.; Miron, Y.; Grandbois, M. Assembly of Collagen Fibril Meshes Using Gold Nanoparticles Functionalized with Tris(Hydroxymethyl)Phosphine-Alanine as Multivalent Cross-linking Agents. J. Mol. Recognit. 2011, 24, 477–482. DOI: https://doi.org/10.1002/jmr.1131.
- Raghuraman, K.; Katti, K. K.; Katti, K. K.; White, H. W.; Cutler, C. S. Methods and Articles for Gold Nanoparticle Production. U.S. Patent 2007/0051202, Mar 8, 2007.
- Kannan, R.; Rahing, V.; Cutler, C.; Pandrapragada, R.; Katti, K. K.; Kattumuri, V.; Robertson, J. D.; Casteel, S. J.; Jurisson, S.; Smith, C.; et al. Nanocompatible Chemistry toward Fabrication of Target-Specific Gold Nanoparticles. J. Am. Chem. Soc. 2006, 128, 11342–11343. DOI: https://doi.org/10.1021/ja063280c.
- Katti, K. K.; Kattumuri, V.; Bhaskaran, S.; Katti, K. V.; Kannan, R. Facile and General Method for Synthesis of Sugar Coated Gold Nanoparticles. Int. J. Green Nanotechnol. Biomed. 2009, 1, B53–B59. DOI: https://doi.org/10.1080/19430850902983848.
- Raghuraman, K.; Katti, K. K. Methods for Producing Silver Nanoparticles. U.S. Patent 9,005,663, Apr 14, 2015.
- Maziero, J. S.; Thipe, V. C.; Rogero, S. O.; Cavalcante, A. K.; Damasceno, K. C.; Ormenio, M. B.; Martini, G. A.; Batista, J. G. S.; Viveiros, W.; Katti, K. K.; et al. Species-Specific in Vitro and in Vivo Evaluation of Toxicity of Silver Nanoparticles Stabilized with Gum Arabic Protein. Int. J. Nanomed. 2020, 15, 7359–7376. DOI: https://doi.org/10.2147/IJN.S250467.
- Jones, C. R.; Collins, G. R. Tanning Leather. Br. Patent 2,384,006, Jul. 16, 2003.
- Janak, K. Process and Compositions for the Removal of Hydrogen Sulfide from Industrial Process Fluids. World Patent 2013/041654, Mar 28, 2013.
- Lanxess Deutcshland, GmbH. Material Mixture Useful as Bleaching Agent for e.g. Bleaching Vegetable Fibers, Comprises Iminodisuccinate and Tris(Hydroxyalkyl)Phosphane and/or Their Derivates and/or Salts. Ger. Patent 20 2005 017 820, Feb 23, 2006.
- Reichel, M.; Unger, C.; Dubovnik, S.; Roidl, A.; Kornath, A.; Karaghiosoff, K. Synthesis, Structural and Toxicological Investigations of Quarternary Phosphonium Salts Containing the P-Bonded Bioisosteric CH2F Moiety. New J. Chem. 2020, 44, 14306–14315. DOI: https://doi.org/10.1039/d0nj02310h.
- Xu, D.; Li, Y.; Gu, T. A Synergistic D-Tyrosine and Tetrakis Hydroxymethyl Phosphonium Sulfate Biocide Combination for the Mitigation of an SRB Biofilm. World J. Microbiol. Biotechnol. 2012, 28, 3067–3074. DOI: https://doi.org/10.1007/s11274-012-1116-0.
- Xu, D.; Li, Y.; Gu, T. D-Methionine as a Biofilm Dispersal Signaling Molecule Enhanced Tetrakis Hydroxymethyl Phosphonium Sulfate Mitigation of Desulfovibrio vulgaris Biofilm and Biocorrosion Pitting. Mater. Corros. 2014, 65, 837–845. DOI: https://doi.org/10.1002/maco.201206894.
- Li, Y.; Jia, R.; Al-Mahamedh, H. H.; Xu, D.; Gu, T. Enhanced Biocide Mitigation of Field Biofilm Consortia by a Mixture of D-Amino Acids. Front. Microbiol. 2016, 7, 896. DOI: https://doi.org/10.3389/fmicb.2016.00896.
- Jia, R.; Yang, D.; Rahman, H. B. A.; Gu, T. Laboratory Testing of Enhanced Biocide Mitigation of an Oilfield Biofilm and Its Microbiologically Influenced Corrosion of Carbon Steel in the Presence of Oilfield Chemicals. Int. Biodeterior. Biodegradation 2017, 125, 116–124. DOI: https://doi.org/10.1016/j.ibiod.2017.09.006.
- Xu, D.; Jia, R.; Li, Y.; Gu, T. Advances in the Treatment of Problematic Industrial Biofilms. World J. Microbiol. Biotechnol. 2017, 33, 97. DOI: https://doi.org/10.1007/s11274-016-2203-4.
- Fytianos, G.; Banti, D.; Dushku, E.; Papastergiadis, E.; Yiangou, M.; Samaras, P. Novel Approaches for Biocorrosion Mitigation in Sewer Systems. Chemistry 2021, 3, 1166–1177. DOI: https://doi.org/10.3390/chemistry3040085.
- Xu, J.; Jia, R.; Yang, D.; Sun, C.; Gu, T. Effects of D-Phenylalanine as a Biocide Enhancer of THPS against the Microbiologically Influenced Corrosion of C1018 Carbon Steel. J. Mater. Sci. Technol. 2019, 35, 109–117. DOI: https://doi.org/10.1016/j.jmst.2018.09.011.
- Eldefrawi, A. T.; Mansour, N. A.; Brattsten, L. B.; Ahrens, V. D.; Lisk, D. J. Further Toxicologic Studies with Commercial and Candidate Flame Retardant Chemicals. Part II. Bull. Environ. Contam. Toxicol. 1977, 17, 720–726. DOI: https://doi.org/10.1007/BF01685960.
- Wyllie, M. J.; Turner, H.; Henderson, W. Tris(Hydroxymethyl)Phosphine, P(CH2OH)3—A Convenient and Effective New Reagent for the Fixation of Protein Samples for SEM Imaging. Micron 2016, 89, 28–33. DOI: https://doi.org/10.1016/j.micron.2016.06.007.
- Ayaz, P.; Li, J.; Jin, W.; Ma, M. Fixation of the Color of Naturally Colored Domestic Silk by Cross-Linking the Sericin with Tetrakis (Hydroxymethyl) Phosphonium Sulfate. Fibers Polym. 2020, 21, 548–554. DOI: https://doi.org/10.1007/s12221-020-9367-0.
- Jirasek, A.; Hilts, M.; Shaw, C.; Baxter, P. Investigation of Tetrakis Hydroxymethyl Phosphonium Chloride as an Antioxidant for Use in X-Ray Computed Tomography Polyacrylamide Gel Dosimetry. Phys. Med. Biol. 2006, 51, 1891–1906. DOI: https://doi.org/10.1088/0031-9155/51/7/018.
- Sedaghat, M.; Bujold, R.; Lepage, M. Severe Dose Inaccuracies Caused by an Oxygen-Antioxidant Imbalance in Normoxic Polymer Gel Dosimeters. Phys. Med. Biol. 2011, 56, 601–625. DOI: https://doi.org/10.1088/0031-9155/56/3/006.
- Sedaghat, M.; Bujold, R.; Lepage, M. Preliminary Studies on the Role and Reactions of Tetrakis(Hydroxymethyl)Phosphonium Chloride in Polyacrylamide Gel Dosimeters. Phys. Med. Biol. 2012, 57, 5981–5994. DOI: https://doi.org/10.1088/0031-9155/57/19/5981.
- Chen, L.; Qiang, T.; Chen, X.; Ren, W.; Zhang, H. J. Fabrication and Evaluation of Biodegradable Multi-Cross-Linked Mulch Film Based on Waste Gelatin. Chem. Eng. Sci. 2021, 419, 129639. DOI: https://doi.org/10.1016/j.cej.2021.129639.
- Gilbert, P. D.; Talbot, R. E. Photographic Hardeners. World Patent 99/22271, May 6, 1999.
- Vaish, A.; Roy, S. G.; De, P. Synthesis of Amino Acid Based Covalently Cross-Linked Polymeric Gels Using Tetrakis(Hydroxymethyl)Phosphonium Chloride as a Cross-Linker. Polymer 2015, 58, 1–8. DOI: https://doi.org/10.1016/j.polymer.2014.12.043.
- Renner, J. N.; Cherry, K. M.; Su, R. S.-C.; Liu, J. C. Characterization of Resilin-Based Materials for Tissue Engineering Applications. Biomacromolecules 2012, 13, 3678–3685. DOI: https://doi.org/10.1021/bm301129b.
- Li, L.; Tong, Z.; Jia, X.; Kiick, K. L. Resilin-Like Polypeptide Hydrogels Engineered for Versatile Biological Functions. Soft Matter. 2013, 9, 665–673. DOI: https://doi.org/10.1039/c2sm26812d.
- Kim, Y.; Gill, E. E.; Liu, J. C. Enzymatic Cross-Linking of Resilin-Based Proteins for Vascular Tissue Engineering Applications. Biomacromolecules 2016, 17, 2530–2539. doi: https://doi.org/10.1021/acs.biomac.6b00500.
- Li, L.; Kiick, K. L. Transient Dynamic Mechanical Properties of Resilin-Based Elastomeric Hydrogels. Front. Chem. 2014, 2, 21. DOI: https://doi.org/10.3389/fchem.2014.00021.
- Li, L.; Stiadle, J. M.; Levendoski, E. E.; Lau, H. K.; Thibeault, S. L.; Kiick, K. L. Biocompatibility of Injectable Resilin-Based Hydrogels. J. Biomed. Mater. Res. A. 2018, 106, 2229–2242. DOI: https://doi.org/10.1002/jbm.a.36418.
- Su, R. S.-C.; Gill, E. E.; Kim, Y.; Liu, J. C. Characterization of Resilin-like Proteins with Tunable Mechanical Properties. J. Mech. Behav. Biomed. Mater. 2019, 91, 68–75. DOI: https://doi.org/10.1016/j.jmbbm.2018.11.015.
- McGann, C. L.; Akins, R. E.; Kiick, K. L. Resilin-PEG Hybrid Hydrogels Yield Degradable Elastomeric Scaffolds with Heterogeneous Microstructure. Biomacromolecules 2016, 17, 128–140. DOI: https://doi.org/10.1021/acs.biomac.5b01255.
- Li, L.; Mahara, A.; Tong, Z.; Levenson, E. A.; McGann, C. L.; Jia, X.; Yamaoka, T.; Kiick, K. L. Recombinant Resilin-Based Bioelastomers for Regenerative Medicine Applications. Adv. Healthc. Mater. 2016, 5, 266–275. DOI: https://doi.org/10.1002/adhm.201500411.
- Lampe, K. J.; Antaris, A. L.; Heilshorn, S. C. Design of Three-Dimensional Engineered Protein Hydrogels for Tailored Control of Neurite Growth. Acta Biomater. 2013, 9, 5590–5599. DOI: https://doi.org/10.1016/j.actbio.2012.10.033.
- Hollingshead, S.; Liu, J. C. pH-Sensitive Mechanical Properties of Elastin-Based Hydrogels. Macromol. Biosci. 2020, 20, 1900369. DOI: https://doi.org/10.1002/mabi.201900369.
- Campos, D. F. D.; Lindsay, C. D.; Roth, J. G.; LeSavage, B. L.; Seymour, A. J.; Krajina, B. A.; Ribeiro, R.; Costa, P. F.; Blaeser, A.; Heilshorn, S. C. Bioprinting Cell- and Spheroid-Laden Protein-Engineered Hydrogels as Tissue-on-Chip Platforms. Front. Bioeng. Biotechnol. 2020, 8, 374. DOI: https://doi.org/10.3389/fbioe.2020.00374.
- Kambe, Y.; Tokushige, T.; Mahara, A.; Iwasaki, Y.; Yamaoka, T. Cardiac Differentiation of Induced Pluripotent Stem Cells on Elastin-like Protein-Based Hydrogels Presenting a Single-Cell Adhesion Sequence. Polym. J. 2019, 51, 97–105. DOI: https://doi.org/10.1038/s41428-018-0110-2.
- LeSavage, B. L.; Suhar, N. A.; Madl, C. M.; Heilshorn, S. C. Production of Elastin-like Protein Hydrogels for Encapsulation and Immunostaining of Cells in 3D. J. Vis. Exp. 2018, 135, e57739. DOI: https://doi.org/10.3791/57739.
- Haugh, M. G.; Vaughan, T. J.; Madl, C. M.; Raftery, R. M.; McNamara, L. M.; O'Brien, F. J.; Heilshorn, S. C. Investigating the Interplay between Substrate Stiffness and Ligand Chemistry in Directing Mesenchymal Stem Cell Differentiation within 3D Macro-Porous Substrates. Biomaterials 2018, 171, 23–33. DOI: https://doi.org/10.1016/j.biomaterials.2018.04.026.
- Paul, A.; Stührenberg, M.; Chen, S.; Rhee, D.; Lee, W.-K.; Odom, T. W.; Heilshorn, S. C.; Enejder, A. Micro- and Nano-Patterned Elastin-Like Polypeptide Hydrogels for Stem Cell Culture. Soft Matter. 2017, 13, 5665–5675. DOI: https://doi.org/10.1039/C7SM00487G.]
- Wang, H.; Paul, A.; Nguyen, D.; Enejder, A.; Heilshorn, S. C. Tunable Control of Hydrogel Microstructure by Kinetic Competition between Self-Assembly and Crosslinking of Elastin-like Proteins. ACS Appl Mater Interfaces 2018, 10, 21808–21815. DOI: https://doi.org/10.1021/acsami.8b02461.
- Chung, C.; Pruitt, B. L.; Heilshorn, S. C. Spontaneous Cardiomyocyte Differentiation of Mouse Embryoid Bodies Regulated by Hydrogel Crosslink Density. Biomater. Sci. 2013, 1, 1082–1090. DOI: https://doi.org/10.1039/C3BM60139K.
- DiMarco, R. L.; Hunt, D. R.; Dewi, R. E.; Heilshorn, S. C. Improvement of Paracellular Transport in the Caco-2 Drug Screening Model Using Protein-Engineered Substrates. Biomaterials 2017, 129, 152–162. DOI: https://doi.org/10.1016/j.biomaterials.2017.03.023.
- Lim, D. W. In-Situ Crosslinkable and Self-Assembling Elastin-like Polypeptide Block Copolymers for Cartilage Tissue Repair. Ph.D. Dissertation, Duke University, Durham, North Carolina, 2007.
- Chiang, M.-Y.; Lo, Y.-C.; Lai, Y.-H.; Yong, Y.-Y. A.; Chang, S.-J.; Chen, W.-L.; Chen, S.-Y. Protein-Based Soft Actuator with High Photo-Response and Easy Modulation for Anisotropic Cell Alignment and Proliferation in a Liquid Environment. J. Mater. Chem. B. 2021, 9, 6634–6645. DOI: https://doi.org/10.1039/D1TB01198G.
- Wang, H.; Cai, L.; Paul, A.; Enejder, A.; Heilshorn, S. C. Hybrid Elastin-Like Polypeptide-Polyethylene Glycol (ELP-PEG) Hydrogels with Improved Transparency and Independent Control of Matrix Mechanics and Cell Ligand Density. Biomacromolecules 2014, 15, 3421–3428. DOI: https://doi.org/10.1021/bm500969d.
- Meco, E.; Lampe, K. J. Impact of Elastin-like Protein Temperature Transition on PEG-ELP Hybrid Hydrogel Properties. Biomacromolecules 2019, 20, 1914–1925. DOI: https://doi.org/10.1021/acs.biomac.9b00113.
- Lau, H. K. Resilin-like Polypetide-Based Microstructured Hydrogels via Aqueous-Based Liquid-Liquid Phase Separation for Tissue Engineering Applications. Ph.D. Dissertation, University of Delaware, U.S., 2018.
- Lau, H. K.; Li, L.; Jurusik, A. K.; Sabanayagam, C. R.; Kiick, K. L. Aqueous Liquid-Liquid Phase Separation of Resilin-Like Polypeptide/Polyethylene Glycol Solutions for the Formation of Microstructured Hydrogels. ACS Biomater. Sci. Eng. 2017, 3, 757–766. DOI: https://doi.org/10.1021/acsbiomaterials.6b00076.
- Lim, D. W.; Nettles, D. L.; Setton, L. A.; Chilkoti, A. In Situ Cross-Linking of Elastin-like Polypeptide Block Copolymers for Tissue Repair. Biomacromolecules 2008, 9, 222–230. DOI: https://doi.org/10.1021/bm7007982.
- Charati, M. B.; Ifkovits, J. L.; Burdick, J. A.; Linhardt, J. G.; Kiick, K. L. Hydrophilic Elastomeric Biomaterials Based on Resilin-Like Polypeptides. Soft Matter. 2009, 5, 3412–3416. DOI: https://doi.org/10.1039/b910980c.
- Ma, L.; Yang, Y.; Yao, J.; Shao, Z.; Huang, Y.; Chen, X. Selective Chemical Modification of Soy Protein for a Tough and Applicable Plant Protein-Based Material. J. Mater. Chem. B 2015, 3, 5241–5248. DOI: https://doi.org/10.1039/C5TB00523J.
- Gonzalez, M. A.; Simon, J. R.; Ghoorchian, A.; Scholl, Z.; Lin, S.; Rubinstein, M.; Marszalek, P.; Chilkoti, A.; López, G. P.; Zhao, X. Strong, Tough, Stretchable, and Self-Adhesive Hydrogels from Intrinsically Unstructured Proteins. Adv. Mater. 2017, 29, 1604743. DOI: https://doi.org/10.1002/adma.201604743.
- Meco, E.; Zheng, W. S.; Sharma, A. H.; Lampe, K. J. Guiding Oligodendrocyte Precursor Cell Maturation with Urokinase Plasminogen Activator-Degradable Elastin-like Protein Hydrogels. Biomacromolecules 2020, 21, 4724–4736. DOI: https://doi.org/10.1021/acs.biomac.0c00828.
- Costa, R. R.; González-Pérez, M.; Herrero-Gutiérrez, M.; Pires, R. A.; Alonso, M.; Rodriguez-Cabello, J. C.; Reis, R. L.; Pashkuleva, I. Tuning the Stiffness of Surfaces by Assembling Genetically Engineered Polypeptides with Tailored Amino Acid Sequence. Biomacromolecules 2018, 19, 3401–3411. DOI: https://doi.org/10.1021/acs.biomac.8b00723.
- Fitch, C. A.; Platzer, G.; Okon, M.; Garcia-Moreno, B.; McIntosh, L. P. Arginine: Its pKa Value Revisited. Protein Sci. 2015, 24, 752–761. DOI: https://doi.org/10.1002/pro.2647.
- Karasik, A. A.; Georgiev, I. O.; Musina, E. I.; Sinyashin, O. G.; Heinicke, J. Synthesis of Novel Water-Soluble Linear and Heterocyclic Phosphino Amino Acids from 2-Phosphinophenols or 2-Phosphinophenolethers, Formaldehyde and Amino Acids. Polyhedron 2001, 20, 3321–3331. DOI: https://doi.org/10.1016/S0277-5387(01)00950-0.
- Sahiner, N. Single Step Poly(l-Lysine) Microgel Synthesis, Characterization and Biocompatibility Tests. Polymer 2017, 121, 46–54. DOI: https://doi.org/10.1016/j.polymer.2017.06.014.
- Sahiner, N. Amino Acid-Derived Poly(L-Lysine) (p(LL)) Microgel as a Versatile Biomaterial: Hydrolytically Degradable, Drug Carrying, Chemically Modifiable and Antimicrobial Material. Polym. Adv. Technol. 2020, 31, 2152–2160. DOI: https://doi.org/10.1002/pat.4936.
- Chilamari, M.; Kalra, N.; Shukla, S.; Rai, V. Single-Site Labeling of Lysine in Proteins Through a Metal-Free Multicomponent Approach. Chem. Commun. 2018, 54, 7302–7305. DOI: https://doi.org/10.1039/C8CC03311K.
- Zhu, L.; Kemple, M. D.; Yuan, P.; Prendergast, F. G. N-Terminus and Lysine Side Chain pKa Values of Melittin in Aqueous Solutions and Micellar Dispersions Measured by 15N NMR. Biochemistry 1995, 34, 13196–13202. DOI: https://doi.org/10.1021/bi00040a035.
- Isom, D. G.; Castañeda, C. A.; Cannon, B. R.; García-Moreno, B. Large Shifts in pKa Values of Lysine Residues Buried inside a Protein. PNAS 2011, 108, 5260–5265. DOI: https://doi.org/10.1073/pnas.1010750108.
- Grimsley, G. R.; Scholtz, J. M.; Pace, C. N. A Summary of the Measured pK Values of the Ionizable Groups in Folded Proteins. Protein Sci. 2009, 18, 247–251. DOI: https://doi.org/10.1002/pro.19.
- Zhou, H.-X.; Vijayakumar, M. Modeling of Protein Conformational Fluctuations in pKa Predictions. J. Mol. Biol. 1997, 267, 1002–1011. DOI: https://doi.org/10.1006/jmbi.1997.0895.
- Andersson, L. K.; Caspersson, M.; Baltzer, L. Control of Lysine Reactivity in Four-Helix Bundle Proteins by Site-Selective pKa Depression: Expanding the Versatility of Proteins by Postsynthetic Functionalisation. Chem. Eur. J. 2002, 8, 3687–3697. DOI: https://doi.org/10.1002/1521-3765(20020816)8:16 < 3687::AID-CHEM3687 > 3.0.CO;2-8.
- Hacker, S. M.; Backus, K. M.; Lazear, M. R.; Forli, S.; Correia, B. E.; Cravatt, B. F. Global Profiling of Lysine Reactivity and Ligandability in the Human Proteome. Nat. Chem. 2017, 9, 1181–1190. DOI: https://doi.org/10.1038/nchem.2826.
- Baeza, J.; Smallegan, M. J.; Denu, J. M. Site-Specific Reactivity of Nonenzymatic Lysine Acetylation. ACS Chem. Biol. 2015, 10, 122–128. DOI: https://doi.org/10.1021/cb500848p.
- Dutta, A.; Roberts, J. A. S.; Shaw, W. J. Arginine-Containing Ligands Enhance H2 Oxidation Catalyst Performance. Angew. Chem. Int. Ed. 2014, 53, 6487–6491. DOI: https://doi.org/10.1002/anie.201402304.
- Sahiner, N. One Step Synthesis of an Amino Acid Derived Particles, Poly(L-Arginine) and Its Biomedical Application. Polym. Adv. Technol. 2021, in press. DOI: https://doi.org/10.1002/pat.5559.
- Kallen, R. G. The Mechanism of Reactions Involving Schiff Base intermediates. Thiazolidine Formation from L-Cysteine and Formaldehyde. J. Am. Chem. Soc. 1971, 93, 6236–6248. DOI: https://doi.org/10.1021/ja00752a040.
- Xia, T.; Jiang, X.; Deng, L.; Yang, M.; Chen, X. Albumin-Based Dynamic Double Cross-Linked Hydrogel with Self-Healing Property for Antimicrobial Application. Colloids Surf. B 2021, 208, 112042. DOI: https://doi.org/10.1016/j.colsurfb.2021.112042.
- Parra, J. L.; Domínguez, J. J. G. Reactividad Química de Las Fibras de Lana Frente a Las so Uciones de THPC y Acido Tioglicólico: Influencia de Los Tensioactivos Iónicos. Investig. Inf. Text. Tensioact 1979, 22, 57–65.
- Kamińska, A.; Chwatko, G. Estimation of Lipoyllysine Content in Meat and Its Antioxidative Capacity. J. Agric. Food Chem. 2020, 68, 10992–10999. DOI: https://doi.org/10.1021/acs.jafc.0c03778.
- Liu, Z.; Tang, Z.; Zhu, L.; Lu, S.; Chen, F.; Tang, C.; Sun, H.; Yang, J.; Qin, G.; Chen, Q. Natural Protein-Based Hydrogels with High Strength and Rapid Self-Recovery. Int. J. Biol. Macromol. 2019, 141, 108–116. DOI: https://doi.org/10.1016/j.ijbiomac.2019.08.258.
- Kubiczek, D.; Flaig, C.; Raber, H.; Dietz, S.; Kissmann, A.-K.; Heerde, T.; Bodenberger, N.; Wittgens, A.; González-Garcia, M.; Kang, F. A Cerberus-Inspired Anti-Infective Multicomponent Gatekeeper Hydrogel against Infections with the Emerging “Superbug” Yeast Candida auris. Macromol. Biosci. 2020, 20, 2000005. DOI: https://doi.org/10.1002/mabi.202000005.
- Favella, P.; Kissmann, A.-K.; Raber, H. F.; Kubiczek, D. H.; Bodenberger, P.; Bodenberger, N. E.; Rosenau, F. Diffusion-Controlled Release of the Theranostic Protein-Photosensitizer Azulitox from Composite of Fmoc-Phenylalanine Fibrils Encapsulated with BSA Hydrogels. J. Biotechnol. 2021, 341, 51–62. DOI: https://doi.org/10.1016/j.jbiotec.2021.08.014.
- Bodenberger, N.; Kubiczek, D.; Halbgebauer, D.; Rimola, V.; Wiese, S.; Mayer, D.; Alfonso, A. A. R.; Ständker, L.; Stenger, S.; Rosenau, F. Lectin-Functionalized Composite Hydrogels for “Capture-and-Killing” of Carbapenem-Resistant Pseudomonas aeruginosa. Biomacromolecules 2018, 19, 2472–2482. DOI: https://doi.org/10.1021/acs.biomac.8b00089.
- Bodenberger, N.; Kubiczek, D.; Abrosimova, I.; Scharm, A.; Kipper, F.; Walther, P.; Rosenau, F. Evaluation of Methods for Pore Generation and Their Influence on Physio-Chemical Properties of a Protein Based Hydrogel. Biotechnol. Rep. 2016, 12, 6–12. DOI: https://doi.org/10.1016/j.btre.2016.09.001.
- Bodenberger, N.; Kubiczek, D.; Rosenau, F. Easy Manipulation of Architectures in Protein-Based Hydrogels for Cell Culture Applications. J. Vis. Exp. 2017, 126, e55813. DOI: https://doi.org/10.3791/55813.
- Bodenberger, N.; Kubiczek, D.; Trösch, L.; Gawanbacht, A.; Wilhelm, S.; Tielker, D.; Rosenau, F. Lectin-Mediated Reversible Immobilization of Human Cells into a Glycosylated Macroporous Protein Hydrogel as a Cell Culture Matrix. Sci. Rep. 2017, 7, 6151. DOI: https://doi.org/10.1038/s41598-017-06240-w.
- Bodenberger, N.; Paul, P.; Kubiczek, D.; Walther, P.; Gottschalk, K.-E.; Rosenau, F. A Novel Cheap and Easy to Handle Protein Hydrogel for 3D Cell Culture Applications: A High Stability Matrix with Tunable Elasticity and Cell Adhesion Properties. Chem. Select. 2016, 1, 1353–1360. DOI: https://doi.org/10.1002/slct.201600206.
- Pakkaner, E. Hydrogels and Self-Assembled Nanostructures Based on Wool Keratose. Ms.D. Dissertation, İzmir Institute of Technology, 2017.
- Bodenberger, N.; Kubiczek, D.; Paul, P.; Preising, N.; Weber, L.; Bosch, R.; Hausmann, R.; Gottschalk, K.-E.; Rosenau, F. Beyond Bread and Beer: Whole Cell Protein Extracts from Baker's Yeast as a Bulk Source for 3D Cell Culture Matrices. Appl. Microbiol. Biotechnol. 2017, 101, 1907–1917. DOI: https://doi.org/10.1007/s00253-016-7982-x.
- Shi, K.; Shao, S.; Yin, W. An Improved Non-Formaldehyde Tissue Preservative. Adv. Mat. Res. 2012, 356-360, 360–363. DOI: https://doi.org/10.4028/www.scientific.net/AMR.356-360.360.
- Jiang, X.; Li, M.; Guo, X.; Chen, H.; Yang, M.; Rasooly, A. Self-Assembled DNA-THPS Hydrogel as a Topical Antibacterial Agent for Wound Healing. ACS Appl. Bio. Mater. 2019, 2, 1262–1269. DOI: https://doi.org/10.1021/acsabm.8b00818.
- Jayawardhana, D. A.; Sengupta, M. K.; Krishantha, D. M. M.; Gupta, J.; Armstrong, D. W.; Guan, X. Chemical-Induced pH-Mediated Molecular Switch. Anal. Chem. 2011, 83, 7692–7697. DOI: https://doi.org/10.1021/ac2019393.
- Cochrane, F. C.; Petach, H. H.; Henderson, W. Application of Tris(Hydroxymethyl)Phosphine as a Coupling Agent for Alcohol Dehydrogenase Immobilization. Enzyme Microb. Technol. 1996, 18, 373–378. DOI: https://doi.org/10.1016/0141-0229(95)00134-4.
- Lu, D.; Yong, K.; Chen, X.; Feng, S. Immobilization of α-Glucosidase with a Novel Coupling Reagent-Tris(Hydroxymethyl)Phosphine. Shipin Kexue 2005, 26, 61–64.
- Cheng, T.-C.; Duan, K.-J.; Sheu, D.-C. Immobilization of β-Fructofuranosidase from Aspergillus japonicus on Chitosan Using Tris(Hydroxymethyl)Phosphine or Glutaraldehyde as a Coupling Agent. Biotechnol. Lett. 2005, 27, 335–338. DOI: https://doi.org/10.1007/s10529-005-0984-x.
- Cheng, T.-C.; Duan, K.-J.; Sheu, D.-C. Application of Tris(Hydroxymethyl)Phosphine as a Coupling Agent for β-Galactosidase Immobilized on Chitosan to Produce Galactooligosaccharides. J. Chem. Technol. Biotechnol. 2006, 81, 233–236. DOI: https://doi.org/10.1002/jctb.1385.
- Chen, W.; Chen, H.; Xia, Y.; Yang, J.; Zhao, J.; Tian, F.; Zhang, H. P.; Zhang, H. Immobilization of Recombinant Thermostable β-Galactosidase from Bacillus stearothermophilus for Lactose Hydrolysis in Milk. J. Dairy Sci. 2009, 92, 491–498. DOI: https://doi.org/10.3168/jds.2008-1618.
- Malhotra, I.; Basir, S. F. Application of Invertase Immobilized on Chitosan Using Glutaraldehyde or Tris(Hydroxymethyl)Phosphine as Cross-Linking Agent to Produce Bioethanol. Appl. Biochem. Biotechnol. 2020, 191, 838–851. DOI: https://doi.org/10.1007/s12010-019-03162-3.
- Chen, S.-C.; Duan, K.-J. Production of Galactooligosaccharides Using β-Galactosidase Immobilized on Chitosan-Coated Magnetic Nanoparticles with Tris(Hydroxymethyl)Phosphine as an Optional Coupling Agent. Int. J. Mol. Sci. 2015, 16, 12499–12512. DOI: https://doi.org/10.3390/ijms160612499.
- Halling, P. J.; Dunnill, P. Magnetic Supports for Immobilized Enzymes and Bioaffinity Adsorbents. Enzym. Microb. Technol. 1980, 2, 2–10. DOI: https://doi.org/10.1016/0141-0229(80)90002-2.
- Huang, Z.-X.; Cao, S.-L.; Xu, P.; Wu, H.; Zong, M.-H.; Lou, W.-Y. Preparation of a Novel Nanobiocatalyst by Immobilizing Penicillin Acylase onto Magnetic Nanocrystalline Cellulose and Its Use for Efficient Synthesis of Cefaclor. Chem. Eng. J. 2018, 346, 361–368. DOI: https://doi.org/10.1016/j.cej.2018.04.026.
- Wu, X.; Xiong, J.; Huang, Z.; Cao, S.; Zong, M.; Lou, W. Improving Biocatalysis of Cefaclor with Penicillin Acylase Immobilized on Magnetic Nanocrystalline Cellulose in Deep Eutectic Solvent Based Co-Solvent. Bioresour. Technol. 2019, 288, 121548. DOI: https://doi.org/10.1016/j.biortech.2019.121548.
- Yang, W.; Zhang, N.; Wang, Q.; Wang, P.; Yu, Y. Development of an Eco-Friendly Antibacterial Textile: Lysozyme Immobilization on Wool Fabric. Bioprocess Biosyst Eng. 2020, 43, 1639–1648. DOI: https://doi.org/10.1007/s00449-020-02356-y.
- Jia, D.-X.; Wang, T.; Liu, Z.-J.; Jin, L.-Q.; Li, J.-J.; Liao, C.-J.; Chen, D.-S.; Zheng, Y.-G. Whole Cell Immobilization of Refractory Glucose Isomerase Using Tris(Hydroxymethyl)Phosphine as Crosslinker for Preparation of High Fructose Corn Syrup at Elevated Temperature. J. Biosci. Bioeng. 2018, 126, 176–182. DOI: https://doi.org/10.1016/j.jbiosc.2018.03.001.
- Jia, D.-X.; Liu, Z.-J.; Xu, H.-P.; Li, J.-L.; Li, J.-J.; Jin, L.-Q.; Cheng, F.; Liu, Z.-Q.; Xue, Y.-P.; Zheng, Y.-G. Asymmetric Synthesis of L-Phosphinothricin Using Thermostable alpha-Transaminase Mined from Citrobacter koseri. J. Biotechnol. 2019, 302, 10–17. DOI: https://doi.org/10.1016/j.jbiotec.2019.06.008.
- Johnson, G. S.; Mucalo, M. R.; Lorier, M. A.; Gieland, U.; Mucha, H. The Processing and Characterization of Animal-Derived Bone to Yield Materials with Biomedical Applications. Part II: Milled Bone Powders, Reprecipitated Hydroxyapatite and the Potential Uses of These Materials. J. Mater. Sci.: Mater. Med. 2000, 11, 725–741. DOI: https://doi.org/10.1023/A1008979929632.
- Zhang, X.-H.; Liu, Z.-Q.; Xue, Y.-P.; Wang, Y.-S.; Yang, B.; Zheng, Y.-G. Production of R-Mandelic Acid Using Nitrilase from Recombinant E. coli Cells Immobilized with Tris(Hydroxymethyl)Phosphine. Appl. Biochem. Biotechnol. 2018, 184, 1024–1035. DOI: https://doi.org/10.1007/s12010-017-2604-3.
- Grekov, L. I.; Vladimtseva, I. V.; Efremenko, V. I.; Chernov, A. B. New Technology for Covalent Immobilization of Biomolecules on Supports. I. Development of Methods for Obtaining Sorbents Based on Tris(Hydroxymethyl)Phosphine. Biotekhnologiya 2007, 34–40.
- Liang, X-x.; Wei, D. Lipase Immobilization with a New Crosslinking Reagent Tris(Hydroxymethyl)Phosphine. Xiandai Shipin Keji 2012, 28, 47–51.
- Bowes, J. H.; Cater, C. W. Crosslinking of Collagen. J. Appl. Chem. 2007, 15, 296–304. DOI: https://doi.org/10.1002/jctb.5010150702.
- Bayramoglu, E. E.; Yorgancioglu, A.; Onem, E. Analysis of Release of Free Formaldehyde Originated from THP Salt Tannages in Leather by High Performance Liquid Chromatography: Origanum Onites Essential Oil as Free Formaldehyde Scavenger. J. Am. Leather Chem. Assoc. 2013, 108, 411–419.
- Onem, E.; Yorgancioglu, A.; Karavana, H. A.; Yilmaz, O. Comparison of Different Tanning Agents on the Stabilization of Collagen via Differential Scanning Calorimetry. J. Therm. Anal. Calorim. 2017, 129, 615–622. DOI: https://doi.org/10.1007/s10973-017-6175-x.
- Shi, J.; Wang, C.; Hu, L.; Xiao, Y.; Lin, W. A Novel Wet-White Tanning Approach Based on Laponite Clay Nanoparticles for Reduced Formaldehyde Release and Improved Physical Performances. ACS Sustainable Chem. Eng. 2019, 7, 1195–1201. DOI: https://doi.org/10.1021/acssuschemeng.8b04845.
- Collins, G. R.; Jones, C. R.; Talbot, R. E.; Williams, J.; Zakikhani, M. Tanning Leather. World Patent 99/23261, May 14, 1999.
- Fathima, N. N.; Rao, J. R.; Nair, B. U. Studies on Phosphonium Based Combination Tanning: Less Chrome Approach. J. Am. Leather Chem. Assoc. 2011, 106, 249–256.
- Ya, L.; Shuangxi, S.; Lan, J.; Kaiqi, S. Rare Earth and Tetra Hydroxymethyl Phosphonium Sulfate Combination Tanning. Adv. Mater. Res. 2012, 479-481, 430–433. DOI: https://doi.org/10.4028/www.scientific.net/AMR.479-481.430.
- Fathima, N. N.; Kumar, T. P.; Kumar, D. R.; Rao, J. R.; Nair, B. U. Wet White Leather Processing: A New Combination Tanning System. J. Am. Leather Chem. Assoc. 2006, 101, 58–65.
- Shi, J.; Zhang, R.; Yang, N.; Zhang, Y.; Mansel, B. W.; Prabakar, S.; Ma, J. Hierarchical Incorporation of Surface-Functionalized Laponite Clay Nanoplatelets with Type I Collagen Matrix. Biomacromolecules 2021, 22, 504–513. DOI: https://doi.org/10.1021/acs.biomac.0c01391.
- Fathima, N. N.; Bose, M. C.; Rao, J. R.; Nair, B. U. Stabilization of Type I Collagen against Collagenases (Type I) and Thermal Degradation Using Iron Complex. J. Inorg. Biochem. 2006, 100, 1774–1780. DOI: https://doi.org/10.1016/j.jinorgbio.2006.06.014.
- Collins, G. R.; Jones, C. R. Waterproofing. B. Patent 2,375,547, Nov 20, 2002.
- Gao, D.; Wang, P.; Shi, J.; Li, F.; Li, W.; Lyu, B.; Ma, J. A Green Chemistry Approach to Leather Tanning Process: Cage-Like Octa(Aminosilsesquioxane) Combined with Tetrakis(Hydroxymethyl)Phosphonium Sulfate. J. Clean. Prod. 2019, 229, 1102–1111. DOI: https://doi.org/10.1016/j.jclepro.2019.05.008.
- Windus, W.; Happich, W. F. A New Tannage—Tetrakis(Hydroxymethyl)Phosphonium Chloride-Resorcinol. J. Am. Leather Chem. Assoc. 1963, 58, 638–645.
- Burrow, R.; Sundah, D. Tanning Leather. World Patent 00/46409, Aug 10, 2000.
- Shao, S.; Shi, K.; Li, Y.; Jiang, L.; Ma, C. Mechanism of Chrome-Free Tanning with Tetra-Hydroxymethyl Phosphonium Chloride. Chin. J. Chem. Eng. 2008, 16, 446–450. DOI: https://doi.org/10.1016/S1004-9541(08)60103-2.
- Qiang, T.; Wang, X.; Wang, X.; Ren, L.; Guo, P. Study on the Improvement of Water Vapor Permeability and Moisture Absorption of Microfiber Synthetic Leather Base by Collagen. Text. Res. J. 2015, 85, 1394–1403. DOI: https://doi.org/10.1177/0040517514545262.
- Coates, H.; Hoye, P. A. T. Chalkley, B. Dyeing Process. Br. Patent 981,098, Jan 20, 1965.
- Britten, P.; Stosic, R. G.; Wood, C. B.; Hudson, A. Recent Advances in Grain Damage Coverage and Color Fastness. J. Am. Leather Chem. Assoc. 2000, 95, 236–242.
- Guthrie, J. D.; Drake, G. L.; Reeves, W. Application of the THPC Flame-Retardant Process to Cotton Fabrics. Am. Dyest. Rep. 1955, 44, P328–P332.
- Weil, E. D.; Levchik, S. V. Flame Retardants in Commercial Use or Development for Textiles. J. Fire Sci. 2008, 26, 243–281. DOI: https://doi.org/10.1177/0734904108089485.
- Drake, G. L.; Reeves, W. A.; Perkins, R. M. Imparting Flame Resistance to Cotton by Chemical Fixation. Am. Dyest. Rep. 1963, 52, 41–44.
- Basch, A.; Nachamowitz, B.; Hasenfratz, S.; Lewin, M. The Chemistry of THPC–Urea Polymers and Relationship to Flame Retardance on Wool and Wool–Polyester Blends. II. Relative Flame-Retardant Efficiency on Wool, Polyester, and Wool-Polyester Blends. J. Polym. Sci. Polym. Chem. Ed. 1979, 17, 39–47. DOI: https://doi.org/10.1002/pol.1979.170170105.
- Klett, M. W.; Das, B. Method of Increasing Heat Resistance of Glass and the Heat Resistant Glass so Produced. Eur. Patent 0,284,950, Oct 5, 1988.
- Claiborne, J. L.; Wagner, G. M. Ammonia Curing Device Dhows Promise in FR Treating of 100% Cotton Yarns. Text. Chem. Color. 1979, 11, 30/15–34/19.
- Fidoe, S. D.; Talbot, R. E.; Jones, C. R.; Gabriel, R. Treatment of Iron Sulphide Deposits. World Patent 02/08127, Jan 31, 2002.
- Aliasgharzadeh, A.; Mohammadi, A.; Farhood, B.; Anaraki, V.; Mohseni, M.; Moradi, H. Improvement of the Sensitivity of PASSAG Polymer Gel Dosimeter by Urea. Radiat. Phys. Chem. 2020, 166, 108470. DOI: https://doi.org/10.1016/j.radphyschem.2019.108470.
- Granzow, A. Kinetic Study of the Reaction of Tetrakis(Hydroxymethyl)Phosphonium Cation with Urea. J. Am. Chem. Soc. 1977, 99, 2648–2652. DOI: https://doi.org/10.1021/ja00450a041.
- Valetdinov, R. K.; Kuznetsov, E. V.; Mikheeva, T. Y. Phosphorus-Containing Polymers Based on Organic Derivatives of Phosphine. 2. Synthesis of Phosphorus-Containing Urea-Formaldehyde Resins. Tr. Kazakhsk. Khim. Tekhnol. Inst. 1969, 40, 119–124.
- Valetdinov, R. K.; Kuznetsov, E. V.; Mikheeva, T. Y. Method of Preparing Phosphorus-Containing Polymers. U.S.S.R. Patent 197,178, May 31, 1967.
- Basch, A.; Zvilichovsky, B.; Hirshmann, B.; Lewin, M. The Chemistry of THPC-Urea Polymers and Relationship to Flame Retardance on Wool and Wool-Polyester Blends. I. Chemistry of THPC-Urea Polymers. J. Polym. Sci. Polym. Chem. Ed. 1979, 17, 27–37. DOI: https://doi.org/10.1002/pol.1979.170170104.
- Albright & Wilson Ltd. Organic Polymeric Compounds and Materials Containing Phosphorous and Nitrogen. Br. Patent 740,269, Nov 9, 1955.
- Xu, M.; Li, X.; Li, B. Synthesis of a Novel Cross-Linked Organophosphorus-Nitrogen Containing Polymer and Its Application in Flame Retardant Epoxy Resins. Fire Mater. 2016, 40, 848–860. DOI: https://doi.org/10.1002/fam.2349.
- Crowe, G. A.; Lynch, C. C. Urea-Formaldehyde Kinetic Studies. J. Am. Chem. Soc. 1948, 70, 3795–3797. DOI: https://doi.org/10.1021/ja01191a075.
- Crowe, G. A.; Lynch, C. C. Polarographic Urea-Formaldehyde Kinetic Studies. J. Am. Chem. Soc. 1949, 71, 3731–3733. DOI: https://doi.org/10.1021/ja01179a040.
- Smythe, L. E. Urea-Formaldehyde Kinetic Studies. II. Factors Influencing Initial Reaction. J. Am. Chem. Soc. 1952, 74, 2713–2715. DOI: https://doi.org/10.1021/ja01131a006.
- de Jong, J. I.; de Jonge, J. The Reaction of Urea with Formaldehyde. Recl. Trav. Chim. Pays-Bas. 2010, 71, 643–660. DOI: https://doi.org/10.1002/recl.19520710704.
- Nair, B. R.; Francis, D. J. Kinetics and Mechanism of Urea-Formaldehyde Reaction. Polymer 1983, 24, 626–630. DOI: https://doi.org/10.1016/0032-3861(83)90118-0.
- Daigle, D. J.; Pepperman, A. B.; Vail, S. L.; Reeves, W. A. Catalyst for THPOH-Amide Finish. Am. Dyest. Rep. 1973, 62, 37, 40, 74–75.
- Pepperman, A. B.; Daigle, D. J.; Vail, S. L. Reaction of Tris(Hydroxymethyl)Phosphine with Substituted Ureas. J. Org. Chem. 1976, 41, 675–678. DOI: https://doi.org/10.1021/jo00866a018.
- Li, S.; Mayernik, R. A. Flame Resistant Fabrics and Process for Making. U.S. Patent 2011/0308022, Dec 22, 2011.
- Albright & Wilson Ltd. Flame-Proofing Agents Derived from Methylol Phosphorus Polymers. Br. Patent 882,993, Nov 22, 1961.
- Coates, H. Process for Improving the Properties of Cellulose Material. Br. Patent 906,314, Sep 19, 1962.
- Gardner, B. C. Flame-Retardant Filaments. Br. Patent 1,299,373, Dec 13, 1972.
- Date, M.; Fukuoka, S. Method and Composition for Imparting Fire-Proofness to Synthetic Shaped Articles. U.S. Patent 3,855,349, 1974.
- Klett, M. W.; Das, B. Polymeric Compositions Having Flame Retardant Properties. U.S. Patent 4,806,620, Feb 21, 1989.
- Hong, Y. S.; Ko, S. W. Flame Retardant Finish of Cotton Fabrics with THPS-Urea Precondensate. J. Korean Fiber Soc. 1992, 29, 901–909.
- Pepperman, A. B.; Daigle, D. J.; Vail, S. L. Tris(Ureidomethyl)Phosphine Oxides. U.S. Patent 4,102,923, Jul 25, 1978.
- Reuter, M.; Orthner, L.; Wolf, E.; Jakob, F. Verfahren zur Herstellung organischer Phosphor-Verbindungen und gegebenenfalls deren Salze. Ger. Patent 1,067,812, Oct 29, 1959.
- Bhatnagar, S.; Gupta, J. C.; Lal, K.; Bhatnagar, H. L. Reaction of Tetrakis(Hydroxymethyl)Phosphonium Chloride with Thioureas. Indian J. Chem., Sect. A. 1978, 16, 356–358.
- Vail, S. L.; Barker, R. H.; Mennitt, P. G. Formation and Identification of cis- and trans-Dihydroxyimidazolidinones from Ureas and Glyoxal. J. Org. Chem. 1965, 30, 2179–2182. DOI: https://doi.org/10.1021/jo01018a015.
- Frank, A. W. Catalysts for THPOH/Amide Resins. Text. Res. J. 1976, 46, 139–143. DOI: https://doi.org/10.1177/004051757604600210.
- Mikroyannidis, J. A.; Tsolis, A. K. Synthesis of Esters of 4-Hydroxy-5-Phosphinyl-2-Imidazolidinone. J. Heterocycl. Chem. 1982, 19, 1179–1183. DOI: https://doi.org/10.1002/jhet.5570190538.
- Petersen, H.; Reuther, W. α‐Ureidoalkylierung von Phosphor(III)‐Verbindungen. Justus Liebigs Ann. Chem. 1973, 766, 58–72. DOI: https://doi.org/10.1002/jlac.19727660108.
- Frank, A. W. Quaternary Phosphonium Salts Bearing Carbamate Groups. U.S. Patent 4,171,448, Oct 16, 1979.
- Frank, A. W. Synthesis of Tris(Aminomethyl)Phosphine Oxide and Its Carbon Dioxide Adduct from Tetrakis(Hydroxymethyl)Phosphonium Salts via Their Methyl Carbamate Derivatives. Can. J. Chem. 1981, 59, 27–33. DOI: https://doi.org/10.1139/v81-005.
- Tan, Z.-W.; Zhang, M.; Guo, H.-Z.; Qiu, J.-J.; Liu, C.-M. Phosphorus-Containing Polymers from THPS. I. Design, Synthesis, and Characterization of Novel Monomer and Polyureas. Des. Monomers Polym. 2014, 17, 762–774. DOI: https://doi.org/10.1080/15685551.2014.918015.
- Loss, R.; Berini, R.; Hiestand, A.; Hofmann, P.; Nachbur, H. Verfahren zum Flammfestmachen von organischem Fasermaterial. Ger. Patent 2,360,723, Jun 20, 1974.
- Frank, A. W. Tris(N-Carbalkoxylaminomethyl)Phosphines. U.S. Patent 4,204,072, May 20, 1980.
- Frank, A. W. Process for the Preparation of Tris(N-Carbalkoxylaminomethyl)Phosphine Oxides and Sulfides. U.S. Patent 4,578,506, Mar 25, 1986.
- Frank, A. W. Tris(N-Carbalkoxylaminomethyl)Phosphine Oxides and Sulfides. U.S. Patent 4,249,017, Feb 3, 1981.
- Tan, Z.-W.; Sun, J.; Wu, C.-Y.; Qiu, J.-J.; Liu, C.-M. Phosphorus-Containing Polymers from THPS. IV: Synthesis and Properties of Phosphorus-Containing Polybenzoxazines as a Green Route for Recycling Toxic Phosphine (PH3) Tail Gas. J. Hazard. Mater. 2017, 322, 540–550. DOI: https://doi.org/10.1016/j.jhazmat.2016.10.021.
- Ma, C.; Yu, B.; Hong, N.; Pan, Y.; Hu, W.; Hu, Y. Facile Synthesis of a Highly Efficient, Halogen-Free, and Intumescent Flame Retardant for Epoxy Resins: Thermal Properties, Combustion Behaviors, and Flame-Retardant Mechanisms. Ind. Eng. Chem. Res. 2016, 55, 10868–10879. DOI: https://doi.org/10.1021/acs.iecr.6b01899.
- Xu, W.; Li, J.; Liu, F.; Jiang, Y.; Li, Z.; Li, L. Study on the Thermal Decomposition Kinetics and Flammability Performance of a Fame-Retardant Leather. J. Therm. Anal. Calorim. 2017, 128, 1107–1116. DOI: https://doi.org/10.1007/s10973-016-5974-9.
- Chance, L. H.; Moreau, J. P.; Drake, G. L. Flame Retardant for Cotton Based on THPOH and Guanazole. J. Coated Fibr. Mater. 1973, 2, 161–172. DOI: https://doi.org/10.1177/152808377300200303.
- Chance, L. H. Process for Treating Organic Textiles with Flame Retardant Polymers Made from Hydroxymethylphosphorus Compounds and Guanazoles. U.S. Patent 3,914,106, Oct. 21, 1975.
- Loewengart, G.; van Duuren, B. L. The Reaction of Guanosine with Tetrakis(Hydroxymethyl)Phosphonium Chloride. Tetrahedron Lett. 1976, 17, 3473–3476. DOI: https://doi.org/10.1016/S0040-4039(00)71333-5.
- Donaldson, D. J.; Drake, G. L.; Beninate, J. V.; Reeves, W. A.; Daigle, D. J. Flame Proofing Textile Treating Composition of Tris(hydroxymethyl)phosphine-Urea Adduct and Polyvinylbromide. U.S. Patent 3,915,915, Oct 28, 1975.
- Donaldson, D. J.; Normand, F. L.; Drake, G. L.; Reeves, W. A. THPC-Cyanamide Flame-Retardant Finish for Sleepwear Cotton. Text. Res. J. 1972, 42, 331–334. DOI: https://doi.org/10.1177/004051757204200605.
- Donaldson, D. J.; Normand, F. L.; Drake, G. L. Effect of pH on THPC-Cyanamide Flame Retardant. Am. Dyest. Rep. 1972, 61, 50–51.
- Nachbur, H.; Maeder, A. Phosphorus-Containing Condensation Products. U.S. Patent 3,994,971, Nov 30, 1976.
- Normand, F. L.; Donaldson, D. J.; Drake, G. L. A Durable Flame Retardant Finish for Cotton Using Cyanamide-THPC Resins. Am. Dyest. Rep. 1970, 59, 46–48.
- Daigle, D. J.; Pepperman, A. B.; Normand, F. L. Synthesis of 3,7-Dicyano-3,5,7-Triaza-1-Phosphabicyclo[3.3.1]Nonane and Derivatives. J. Heterocycl. Chem. 1972, 9, 715–716. DOI: https://doi.org/10.1002/jhet.5570090341.
- Daigle, D. J.; Pepperman, A. B.; Normand, F. L. Increasing Flame Retardance of Cellulose Textile with 1,3,7-Triaza-5-phosphabicyclo(3.3.1)nonane-3,7-dicarbonitrile. U.S. Patent 3,865,618, Feb 11, 1975.
- Trefonas, L. M.; Brown, J. N. The Crystal and Molecular Structure of 3,7-Dicyano-3,5,7-triaza-1-phosphabicyclo[3.3.1]nonane. J. Heterocycl. Chem. 1972, 9, 1295–1298. DOI: https://doi.org/10.1002/jhet.5570090620.
- Reeves, W. A. Some New Techniques in Cotton Finishing. Am. Dyest. Rep. 1968, 57, 37-41 (P107–P111.
- Reeves, W. A.; Perkins, R. M.; Drake, G. L. Flame Resistant Cellulosic Materials. U.S. Patent 3,276,897, Oct 4, 1966.
- Chance, L. H.; Drake, G. L.; Reeves, W. A. Process for Flameproofing Cellulosic Materials. U.S. Patent 3,404,022, Oct 1, 1968.
- Moiseev, D. V.; Patrick, B. O.; James, B. R. Reactions of Tertiary Phosphines with Alcohols in Aqueous Media. Inorg. Chem. 2009, 48, 239–245. DOI: https://doi.org/10.1021/ic801657g.
- Castellanos-Soriano, J.; Ekubo, A. T.; Elsegood, M. R. J.; Lastra-Calvo, N.; Mantry, A.; Martinez-Insua-Rodriguez, A.; Penarrubia-Ferrer, M. A.; Smith, M. B. Synthesis and Characterization of New Tetraalkylaminophosphonium Chlorides. Phosphorus Sulfur Silicon Relat. Elem. 2017, 192, 570–575. DOI: https://doi.org/10.1080/10426507.2017.1284836.
- Frank, A. W.; Drake, G. L. Aniline Derivatives of Tetrakis(Hydromethyl)Phosphonium Chloride. J. Org. Chem. 1972, 37, 2752–2755. DOI: https://doi.org/10.1021/jo00982a030.
- Frank, A. W.; Drake, G. L. Fireproofing Cellulose Textiles with Tetrakis(hydroxymethyl)phosphonium Chloride and Aniline. U.S. Patent 3,897,205, Jul 29, 1975.
- Nikonov, G. N.; Balueva, A. S.; Erastov, O. A.; Arbuzov, B. A. Reactions of Boryloxymethyl- and Hydroxymethylphosphines with Amines. Russ. Chem. Bull. 1989, 38, 1223–1226. DOI: https://doi.org/10.1007/BF00957157.
- Carpenter-Warren, C. L.; Cunnington, M.; Elsegood, M. R. J.; Kenny, A.; Hill, A. R.; Miles, C. R.; Smith, M. B. Synthesis, Metal Coordination and Structural Studies of Trisubstituted P{CH2-1-N(H)naphthyl}3 Ligands. Inorg. Chim. Acta. 2017, 462, 289–297. DOI: https://doi.org/10.1016/j.ica.2017.03.024.
- Ma, M.; Wang, R. Ionic Covalent Organic Framework Material, Preparation Method, and Solid Composite Electrolyte. Chin. Patent 110423359, Nov 8, 2019.
- Zope, I. S.; Foo, S.; Seah, D. G. J.; Akunuri, A. T.; Dasari, A. Development and Evaluation of a Water-Based Flame Retardant Spray Coating for Cotton Fabrics. ACS Appl. Mater. Interfaces 2017, 9, 40782–40791. DOI: https://doi.org/10.1021/acsami.7b09863.
- Huang, S.; Yang, E.; Yao, J.; Chu, X.; Liu, Y.; Xiao, Q. Nitrogen, Phosphorus and Sulfur Tri-Doped Carbon Dots Are Specific and Sensitive Fluorescent Probes for Determination of Chromium(VI) in Water Samples and in Living Cells. Mikrochim. Acta. 2019, 186, 851. DOI: https://doi.org/10.1007/s00604-019-3941-4.
- Li, J.; Huang, H.; Cao, X.; Wu, H.-H.; Pan, K.; Zhang, Q.; Wu, N.; Liu, X. Template-Free Fabrication of MoP Nanoparticles Encapsulated in N-Doped Hollow Carbon Spheres for Efficient Alkaline Hydrogen Evolution. Chem. Eng. J. 2021, 416, 127677. DOI: https://doi.org/10.1016/j.cej.2020.127677.
- Keen, A. L.; Doster, M.; Han, H.; Johnson, S. A. Facile Assembly of a Cu9 Amido Complex: A New Tripodal Ligand Design That Promotes Transition Metal Cluster Formation. Chem. Commun. 2006, 1221–1223. DOI: https://doi.org/10.1039/b517531c.
- Han, H.; Elsmaili, M.; Johnson, S. A. Diligating Tripodal Amido-Phosphine Ligands: The Effect of a Proximal Antipodal Early Transition Metal on Phosphine Donor Ability in a Building Block for Heterometallic Complexes. Inorg. Chem. 2006, 45, 7435–7445. DOI: https://doi.org/10.1021/ic060692d.
- Raturi, R.; Lefebvre, J.; Leznoff, D. B.; McGarvey, B. R.; Johnson, S. A. A Phosphine-Mediated through-Space Exchange Coupling Pathway for Unpaired Electrons in a Heterobimetallic Lanthanide-Transition Metal Complex. Chemistry 2008, 14, 721–730. DOI: https://doi.org/10.1002/chem.200700355.
- Hatnean, J. A.; Raturi, R.; Lefebvre, J.; Leznoff, D. B.; Lawes, G.; Johnson, S. A. Assembly of Triangular Trimetallic Complexes by Triamidophosphine Ligands: Spin-Frustrated Mn2+ Plaquettes and Diamagnetic Mg2+ Analogues with a Combined through-Space, through-Bond Pathway for 31P-31P Spin-Spin Coupling. J. Am. Chem. Soc. 2006, 128, 14992–14999. DOI: https://doi.org/10.1021/ja065597i.
- Han, H.; Johnson, S. A. Ligand Design for the Assembly of Polynuclear Complexes: Syntheses and Structures of Trinuclear and Tetranuclear Aluminum Alkyl Complexes Bearing Tripodal Diamidoselenophosphinito Ligands and a Comparison to Related Tripodal Triamidophosphine Complexes. Organometallics 2006, 25, 5594–5602. DOI: https://doi.org/10.1021/om0607447.
- Han, H.; Johnson, S. A. Bridged Dinuclear Tripodal Tris(Amido)Phosphane Complexes of Titanium and Zirconium as Diligating Building Blocks for Organometallic Polymers. Eur. J. Inorg. Chem. 2008, 471–482. DOI: https://doi.org/10.1002/ejic.200701015.
- Hatnean, J. A.; Johnson, S. A. Diamagnetic Molybdenum Nitride Complexes Supported by Diligating Tripodal Triamido-Phosphine Ligands as Precursors to Paramagnetic Phosphine Donors. Dalton Trans. 2015, 44, 14925–14936. DOI: https://doi.org/10.1039/C5DT01415H.
- Kisanga, P.; Verkade, J. The Synthesis of 2,6,7-Trioxa-1,4-Diphosphabicyclo[2.2.2]Octane Revisited: The Synthesis of 2,6,7-Triphenyl-2N,6N,7N-Triaza-1,4-Diphosphabicyclo[2.2.2]Octane and the Synthesis of 1λ5-Phosphiranol. Heteroatom Chem. 2001, 12, 114–117. DOI: https://doi.org/10.1002/hc.8.
- Erastov, O. A.; Nikonov, G. N.; Arbuzov, B. A. Alkylation of Aminomethyl Derivatives of Primary Phosphines. Russ. Chem. Bull. 1983, 32, 1250–1254. DOI: https://doi.org/10.1007/BF00953167.
- Liu, C.; Huang, J.; Zhu, J.; Yuan, C.; Zeng, B.; Chen, G.; Xu, Y.; Dai, L. Synthesis of a Novel Azaphosphorine Flame Retardant and Its Application in Epoxy Resins. J. Appl. Polym. Sci. 2018, 135, 45721. DOI: https://doi.org/10.1002/app.45721.
- Frank, A. W.; Drake, G. L. Disproportionation of Tetrakis(Anilinomethyl)Phosphonium Chloride in Ethanol. J. Org. Chem. 1977, 42, 4125–4127. DOI: https://doi.org/10.1021/jo00445a029.
- Zagumennov, V. A.; Karasik, A. A. Electrooxidation of 1,3-Di(para-Tolyl)-5-para-Toluidinomethyl-1,3,5-Diazaphosphorinane on Soluble Metallic Anodes. Phosphorus Sulfur Silicon Relat. Elem. 2018, 193, 50–52. DOI: https://doi.org/10.1080/10426507.2017.1390458.
- Zagumennov, V. A.; Karasik, A. A.; Nikitin, E. V.; Nikonov, G. N. Transformations of 1,3-Di-p-Tolyl-5-p-Toluidinomethyl-1,3,5-Diazaphosphorinane Initiated by Electrochemical Oxidation at a Glassy Carbon Electrode. Russ. Chem. Bull. 1997, 46, 1154–1157. DOI: https://doi.org/10.1007/BF02496218.
- Zagumennov, V. A.; Karasik, A. A. Anodic Oxidation of 1,3-Di(Paratolyl)-5-Paratoluidinomethyl-1,3,5-Diazaphosphorinane on Aluminum. Russ. J. Electrochem. 2014, 50, 1102–1104. DOI: https://doi.org/10.1134/S1023193514110123.
- Zagumennov, V. A.; Karasik, A. A.; Nikitin, E. V.; Nikonov, G. N. Anodic Oxidation of 1,3-Di(para-Tolyl)-5-para-Toluidinomethyl-1,3,5-Diazaphosphorinane. Zh. Obshch. Khim. 1999, 69, 923–927.
- Karasik, A. A. Cyclic β-Heteroatomic Phosphines in the Coordination Chemistry of Transition Metals. Habilitation Dissertation, A. E. Arbuzov Institute of Organic and Physical Chemistry, Russian Federation, Kazan, 2003.
- Beninate, J. V.; Boylston, E. K.; Drake, G. L.; Reeves, W. A. Application of a New Phosphonium Flame Retardant. Am. Dyest. Rep. 1968, 57, 74/P981–978/P985.
- Harper, R. J.; Calamari, T. A.; Schreiber, S. P. Transfer Techniques for Producing Flame Retardant Cotton Fabrics. U.S. Patent 4,194,032, Mar 18, 1980.
- Elgal, G. M.; Perkins, R. M.; Knoepfler, N. B. Prepolymer Preparation and Polymerization of Flame Retardant Chemicals in Cotton. In Solvent Spun Rayon, Modified Cellulose Fibers and Derivatives; Turbak, A., Ed.; American Chemical Society: Washington, DC, 1977; Vol. 58, pp 249–260. DOI: https://doi.org/10.1021/bk-1977-0058.ch017.
- Elgal, G. M.; Drake, G. L. Flame Retardant THP-Prepolymer Application for Shingles. Ind. Eng. Chem. Prod. Res. Dev. 1984, 23, 441–445. DOI: https://doi.org/10.1021/i300015a022.
- Odell, B.; Jones, C. R.; Talbot, R. E. Leaching Divalent Metal Salts. World Patent 00/21892, Apr 20, 2000.
- Deeley, S. E, Dimensional Stabilization of Cellulose Materials. U.S. Patent 3,084,072, Apr 2, 1963.
- Elgal, G. M.; Perkins, R. M.; Knoepfler, N. B. Prepolymer Preparation and Polymerization of Flame Retardant Chemicals from THP-Salts. U.S. Patent 4,246,031, Jan 20, 1981.
- Donaldson, D. J.; Daigle, D. J. Phosphorus-Nitrogen Flame Retardant via Copper Complex. Text. Res. J. 1969, 39, 363–367. DOI: https://doi.org/10.1177/004051756903900411.
- LeBlanc, R. B.; LeBlanc, D. A. Fire Retarding Textile Materials. U.S. Patent 3,957,881, May 18, 1976.
- LeBlanc, R. B.; LeBlanc, D. A. THPS-Ammonia Precondensate Flame-Retardant for Poly/Cot Blends. Am. Dyest. Rep. 1985, 74, 35–40.
- Frank, A. W.; Drake, G. L. Use of Aldehydes Other than Formaldehyde in THPOH/Ammonia Flame-Retardant Finishes for Cotton. J. Appl. Polym. Sci. 1977, 21, 3087–3097. DOI: https://doi.org/10.1002/app.1977.070211120.
- Ricoux, Q.; Bocokić, V.; Méricq, J. P.; Bouyer, D.; von Zutphen, S.; Faur, C. Selective Recovery of Palladium Using an Innovative Functional Polymer Containing Phosphine Oxide. Chem. Eng. J. 2015, 264, 772–779. DOI: https://doi.org/10.1016/j.cej.2014.11.139.
- Ricoux, Q.; Méricq, J. P.; Bouyer, D.; Bocokić, V.; Hernandez-Juarez, L. C.; van Zutphen, S.; Faur, C. A Selective Dynamic Sorption-Filtration Process for Separation of Pd(II) Ions Using an Aminophosphine Oxide Polymer. Sep. Purif. Technol. 2017, 174, 159–165. DOI: https://doi.org/10.1016/j.seppur.2016.10.025.
- Wagner, G. M.; Hoch, P. E.; Gordon, I. Polymerization Inhibitors for Hydroxy Phosphonium Halides Containing Nitrogen Compound Accelerator. U.S. Patent 3,146,212, Aug 25, 1964.
- Hooper, G.; Nakajima, W. N.; Herbes, W. F. The Use of Various Phosphonium Salts for Flame Retardancy by the Ammonia Cure Technique. J. Coated Fabrics 1976, 6, 105–120. DOI: https://doi.org/10.1177/152808377600600208.
- Daigle, D. J.; Donaldson, D. J. Formaldehyde: The Key to Polymerization between THPOH and NH4OH. J. Appl. Polym. Sci. 1970, 14, 248–249. DOI: https://doi.org/10.1002/app.1970.070140124.
- Van Zutphen, S.; Bocokic, V. Method for Preparing Trishydroxymethyl Phosphine. Eur. Patent 2,851,370, Mar 25, 2015.
- Daigle, D. J.; Pepperman, A. B.; Vail, S. L. Synthesis of a Monophosphorus Analog of Hexamethylenetetramine. J. Heterocyclic Chem. 1974, 11, 407–408. DOI: https://doi.org/10.1002/jhet.5570110326.
- Daigle, D. J.; Pepperman, A. B.; Vail, S. L. 1,3,5-Triaza-7-Phosphaadamantane and Derivatives as Flame Retardants for Textiles. U.S. Patent 3,899,619, Aug 12, 1975.
- Daigle, D. J.; Pepperman, A. B. Chemical Proof for the Preferred Nitrogen Quarternization in 1,3,5‐Triaza‐7‐Phosphaadamantane. J. Heterocyclic Chem. 1975, 12, 579–580. DOI: https://doi.org/10.1002/jhet.5570120328.
- Daigle, D. J.; Decuir, T. J.; Robertson, J. B.; Darensbourg, D. J. 1,3,5-Triaza-7-Phosphatricyclo[3.3.1.13,7]Decane and Derivatives. In Inorganic Syntheses; Darensbourg, M. Y., Ed.; John Wiley & Sons: New York, 1998; Vol. 32, pp 40–45. DOI: https://doi.org/10.1002/9780470132630.ch6.
- Carlson, R. D.; Takahashi, A. Composition Comprising Phenolic Resins and Curing Amounts Triaza Phosphaadamantane Compounds. U.S. Patent 4,056,512, Nov 1, 1977.
- Zamisa, S. J. Synthesis, Spectroscopic and Structural Elucidation of Discrete, One Dimensional and Two Dimensional Coordination Compounds of 1,3,5-Triaza-7-Phosphaadamantane, N-Methyl-1,3,5-Triaza-7-Phosphaadamantane and Silver(I). M.Sc. Dissertation, University of KwaZulu-Natal, Durban, South Africa, 2014.
- Bhilare, S.; Kori, S.; Shet, H.; Balaram, G.; Mahendar, K.; Sanghvi, Y. S.; Kapdi, A. R. Scale-Up of a Heck Alkenylation Reaction: Application to the Synthesis of an Amino-Modifier Nucleoside ‘Ruth Linker’. Synthesis 2020, 52, 3595–3603. DOI: https://doi.org/10.1055/s-0040-1707260.
- Fluck, E.; Förster, J. E. Monophosphaurotropin (1,3,5-Triaza-7-Phosphaadamantan) und Einige Derivate. Chemiker Ztg. 1975, 99, 246–247.
- Fisher, K. J.; Alyea, E. C.; Shahnazarian, N. A 31P NMR Study of the Water Soluble Derivatives of 1,3,5-Triaza-7-Phosphaadamantane (PTA). Phosphorus Sulfur Silicon Relat. Elem. 1990, 48, 37–40. DOI: https://doi.org/10.1080/10426509008045879.
- Darensbourg, D. J.; Robertson, J. B.; Larkins, D. L.; Reibenspies, J. H. Water-Soluble Organometallic Compounds. 7. Further Studies of 1,3,5-Triaza-7-Phosphaadamantane Derivatives of Group 10 Metals, Including Metal Carbonyls and Hydrides. Inorg. Chem. 1999, 38, 2473–2481. DOI: https://doi.org/10.1021/ic981243j.
- Gossens, C.; Dorcier, A.; Dyson, P. J.; Rothlisberger, U. pKa Estimation of Ruthenium(II)-Arene PTA Complexes and Their Hydrolysis Products via a DFT/Continuum Electrostatics Approach. Organometallics 2007, 26, 3969–3975. DOI: https://doi.org/10.1021/om700364s.
- Lee, W.-C.; Sears, J. M.; Enow, R. A.; Eads, K.; Krogstad, D. A.; Frost, B. J. Hemilabile β-Aminophosphine Ligands Derived from 1,3,5-Triaza-7-Phosphaadamantane: Application in Aqueous Ruthenium Catalyzed Nitrile Hydration. Inorg. Chem. 2013, 52, 1737–1746. DOI: https://doi.org/10.1021/ic301160x.
- Bravo, J.; Bolaño, S.; Gonsalvi, L.; Peruzzini, M. Coordination Chemistry of 1,3,5-Triaza-7-Phosphaadamantane (PTA) and Derivatives. Part II. The Quest for Tailored Ligands, Complexes and Related Applications. Coord. Chem. Rev. 2010, 254, 555–607. DOI: https://doi.org/10.1016/j.ccr.2009.08.006.
- Guerriero, A.; Peruzzini, M.; Gonsalvi, L. Coordination Chemistry of 1,3,5-Triaza-7-Phosphatricyclo[3.3.1.1]Decane (PTA) and Derivatives. Part III. Variations on a Theme: Novel Architectures, Materials and Applications. Coord. Chem. Rev. 2018, 355, 328–361. DOI: https://doi.org/10.1016/j.ccr.2017.09.024.
- Scalambra, F.; Lorenzo-Luis, P.; de los Ríos, I.; Romerosa, A. New Findings in Metal Complexes with Antiproliferative Activity Containing 1,3,5-Triaza-7-Phosphaadamantane (PTA) and Derivative Ligands. Eur. J. Inorg. Chem. 2019, 1529–1538. DOI: https://doi.org/10.1002/ejic.201801426.
- Tada, H. Decomposition Reaction of Hexamine by Acid. J. Am. Chem. Soc. 1960, 82, 255–263. DOI: https://doi.org/10.1021/ja01487a001.
- Madsen, G. L. Study of the Hexamethylenetetramine, Ammonia, and Formaldehyde System: Quantitative Determination. Ph.D. Dissertation, Loyola University of Chicago, Chicago, Illinois, 1992.
- Fluck, E.; Förster, J.-E.; Weidlein, J.; Hadicke, E. 1,3,5-Triaza-7-Phosphaadamantane (Monophospha-Urotropine). Z. Naturforsch. B. 1977, 32, 499–506. DOI: https://doi.org/10.1515/znb-1977-0505.
- Cashen, N. A. Isolation and Qualitative Characterization of Some of the Water-Soluble by-Products of THPOH-Ammonia Polymer Synthesis. Text. Res. J. 1975, 45, 542–547. DOI: https://doi.org/10.1177/004051757504500706.
- Assmann, B.; Angermaier, K.; Schmidbaur, H. Synthesis, Structure and Complexes of a New Bicyclic N,P-Ligand Derived from Phosphatriazaadamantane. J. Chem. Soc., Chem. Commun. 1994, 941–942. DOI: https://doi.org/10.1039/c39940000941.
- Assmann, B.; Angermaier, K.; Paul, M.; Riede, J.; Schmidbaur, H. Synthesis of 7-Alkyl/Aryl-1,3,5-Triaza-7-Phosphonia-Adamantane Cations and Their Reductive Cleavage to Novel N-Methyl-P-Alkyl/Aryl[3.3.1]Bicyclononane Ligands. Chem. Ber. 1995, 128, 891–900. DOI: https://doi.org/10.1002/cber.19951280907.
- Caporali, M.; Gonsalvi, L.; Zanobini, F.; Peruzzini, M.; Putman, R. D.; Rauchfuss, T. B. Synthesis of the Water-Soluble Bidentate (P,N) Ligand PTN(Me) (PTN(Me) = 7-Phospha-3-Methyl-1,3,5-Triazabicyclo[3.3.1]nonane). In Inorganic Syntheses; Rauchfuss, T. B., Ed.; John Wiley & Sons: Hoboken, NJ, 2010; Vol. 35, pp 96–102. DOI: https://doi.org/10.1002/9780470651568.ch5.
- Frank, A. W.; Daigle, D. J. Triacidic Salts of Tris(Aminomethyl)Phosphines and Their Oxides. Phosphorus Sulfur Relat. Elem. 1981, 10, 255–259. DOI: https://doi.org/10.1080/03086648108077514.
- Huang, R.; Frost, B. J. Development of a Series of P(CH2N = CHR)3 and Trisubstituted 1,3,5-Triaza-7-Phosphaadamantane Ligands. Inorg. Chem. 2007, 46, 10962–10964. DOI: https://doi.org/10.1021/ic701864g.
- Weeden, J. A. Organic and Organometallic Catalysts for Aqueous Nitrile Hydration and Carbon-Carbon Bond Forming Reactions. Ph.D. Dissertation, University of Nevada, Reno, Nevada, 2013.
- Szolnoki, C. T.; Papp, G.; Horváth, H.; Joó, F.; Kathó, Á.; Udvardy, A. Triprotonated 1,3,5-Triaza-7-Phosphaadamantane (PTA); Fantasy or Real Intermediate on Way from PTA to Tetradentate Tris(Aminomethyl)Phosphine? Phosphorus Sulfur Silicon Relat. Elem. in press. DOI: https://doi.org/10.1080/10426507.2021.2014488.
- Siele, V. I. Some Reactions of 1,3,5-Triaza-7-Phosphaadamantane and Its 7-Oxide. J. Heterocycl. Chem. 1977, 14, 337–339. DOI: https://doi.org/10.1002/jhet.5570140238.
- Darensbourg, D. J.; Ortiz, C. G.; Kamplain, J. W. A New Water-Soluble Phosphine Derived from 1,3,5-Triaza-7-Phosphaadamantane (PTA), 3,7-Diacetyl-1,3,7-Triaza-5-Phosphabicyclo[3.3.1]Nonane. Structural, Bonding, and Solubility Properties. Organometallics 2004, 23, 1747–1754. DOI: https://doi.org/10.1021/om0343059.
- Marvelli, L.; Ferretti, V.; Bertolasi, V.; Lampronti, I.; Gambari, R.; Trapella, C.; Turrin, G.; Bonotto, F.; Moriello, A.; Bergamini, P. A New Amido-Phosphine of Dichloroacetic Acid as an Active Ligand for Metals of Pharmaceutical Interest. Synthesis, Characterization and Tests of Antiproliferative and Pro-Apoptotic Activity. J. Inorg. Biochem. 2019, 199, 110787. DOI: https://doi.org/10.1016/j.jinorgbio.2019.110787.
- Weeden, J. A.; Huang, R.; Galloway, K. D.; Gingrich, P. W.; Frost, B. J. The Suzuki Reaction in Aqueous Media Promoted by P, N ligands. Molecules 2011, 16, 6215–6231. DOI: https://doi.org/10.3390/molecules16086215.
- Daigle, D. J.; Pepperman, A. B.; Boudreaux, G. Phosphadamantanes. Synthesis of 2-Thia-1,3,5-Triaza-7-Phosphaadamantane-2,2-Dioxide and Derivatives. J. Heterocyclic Chem. 1974, 11, 1085–1086. DOI: https://doi.org/10.1002/jhet.5570110644.
- Daigle, D. J.; Pepperman, A. B.; Boudreaux, G. J. Process for Flameproofing Cellulosic Textiles. U.S. Patent 3,899,618, Aug 12, 1975.
- Darensbourg, D. J.; Yarbrough, J. C.; Lewis, S. J. 2-Thia-1,3,5-Triaza-7-Phosphaadamantane 2,2-Dioxide (PASO2). Comparative Structural and Reactivity Investigation with the Water-Soluble Phosphine Ligand 1,3,5-Triaza-7-Phosphaadamantane (PTA). Organometallics 2003, 22, 2050–2056. DOI: https://doi.org/10.1021/om0300225.
- Benhammou, M.; Kraemer, R.; Germa, H.; Majoral, J.-P.; Navech, J. Etude de la Reactivite de Quelques Phosphor(III)Adamantanes. Phosphorus Sulfur Relat. Elem. 1982, 14, 105–119. DOI: https://doi.org/10.1080/03086648208073116.
- Navech, J.; Kraemer, R.; Majoral, J.-P. Reactivite de Quelques Phosphor(III)Adamantanes et de Quelques Analogues Tricycliques. Tetrahedron Lett. 1980, 21, 1449–1452. DOI: https://doi.org/10.1016/S0040-4039(00)92742-4.
- Daigle, D. J.; Pepperman, A. B. Synthesis of a Triazaphosphahomoadamantane. J. Chem. Eng. Data 1975, 20, 448–449. DOI: https://doi.org/10.1021/je60067a024.
- Gilbert, P. D.; Grech, J. M.; Talbot, R. E.; Veale, M. A.; Hernandez, K. TetrakisHydroxymethylPhosphonium Sulfate (THPS) for Dissolving Iron Sulfides Downhole and Topsides - A Study of the Chemistry Influencing Dissolution. Presented at CORROSION 2002, Denver, CO, April 7-11, 2002; Paper No. 02030.
- Wang, Q.; Shen, S.; Badairy, H.; Shafai, T.; Jeshi, Y.; Chen, T.; Chang, F. F. Laboratory Assessment of Tetrakis(Hydroxymethyl)Phosphonium Sulfate as Dissolver for Scales Formed in Sour Gas Wells. Int. J. Corros. Scale Inhib. 2015, 4, 235–254. DOI: https://doi.org/10.17675/2305-6894-2015-4-3-235-254.
- Jawish, M. W.; Suleiman, R.; Wang, Q.; Chen, T.; Shen, S. W. New Formulations for the Control of Iron Sulfide Deposits in Oil Production Facilities. Presented at SPE Kingdom of Saudi Arabia Annual Technical Symposium and Exhibition, Dammam, Saudi Arabia, April 23-26, 2018; Paper No. SPE-192228-MS. DOI: https://doi.org/10.2118/192228-MS.
- Patel, D.; Ramanathan, R.; Nasr-El-Din, H. A. Optimization and Thermal Stability of the THPS and NH4Cl Blend to Dissolve Iron Sulfide FeS Scale at HPHT Conditions. Presented at Abu Dhabi International Petroleum Exhibition & Conference, Abu Dhabi, UAE, Nov 11-14, 2019; Paper SPE-197632-MS. DOI: https://doi.org/10.2118/197632-MS.
- Jeffery, J. C.; Odell, B.; Stevens, N.; Talbot, R. E. Self Assembly of a Novel Water Soluble Iron(II) Macrocyclic Phosphine Complex from Tetrakis(Hydroxymethyl)Phosphonium Sulfate and Iron(II) Ammonium Sulfate: Single Crystal X-Ray Structure of the Complex [Fe(H2O)2{RP(CH2N(CH2PR2)CH2)2PR}]SO4•4H2O (R = CH2OH). Chem. Commun. 2000, 101–102. DOI: https://doi.org/10.1039/a908309j.
- Chen, L.; Wang, M.; Han, K.; Zhang, P.; Gloaguen, F.; Sun, L. A Super-Efficient Cobalt Catalyst for Electrochemical Hydrogen Production from Neutral Water with 80 mV Overpotential. Energy Environ. Sci. 2014, 7, 329–334. DOI: https://doi.org/10.1039/C3EE42194E.
- Burrows, A. D.; Dodds, D.; Kirk, A. S.; Lowe, J. P.; Mahon, M. F.; Warren, J. E.; Whittlesey, M. K. Substitution and Derivatization Reactions of a Water Soluble Iron(II) Complex Containing a Self-Assembled Tetradentate Phosphine Ligand. Dalton Trans. 2007, 570–580. DOI: https://doi.org/10.1039/B614726G.
- Lin, C.; Kai, H.; Licheng, S.; Mei, W.; Peili, Z. Cobalt Complex, Preparation Method thereof and Application of Cobalt Complex in Electrochemical Water Reduction to Generate Hydrogen. Chin. Patent 103012496, Apr 3, 2013.
- Khardin, A. P.; Tuzhikov, O. I.; Grekov, L. I.; Valetdinov, R. K.; Pankov, V. I.; Matveeva, E. V.; Nazarova, G. V.; Popov, B. N.; Chuvashov, D. D. Tris(hydroxymethyl)phosphine. U.S.S.R. Patent 1,145,022, Mar 15, 1985.
- Grekov, L. I.; Golovanchikov, A. B.; Litinskii, A. O. Method for Preparation of Tris(hydroxymethyl)phosphine. Rus. Patent 2,366,660, Sep 10, 2009.
- O Kawa, H.; Yoshida, Y.; Otsubo, K.; Kitagawa, H. Network-Selectivity, Magnetism, and Proton Conduction of 2-D and 3-D Metal-Organic Frameworks of the Constituents {P(CH2OH)4}+/MII (MnII, FeII, or CoII)/[CrIII(Ox)3]3. Inorg. Chem. 2020, 59, 623–628. DOI: https://doi.org/10.1021/acs.inorgchem.9b02861.