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Research Article

2-Phenoxyethyldiphenylphosphine oxide as an equivalent of diphenylvinylphosphine oxide in nucleophilic additions

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Pages 902-910 | Received 03 Dec 2020, Accepted 23 May 2021, Published online: 21 Jun 2021

References

  • Kabachnik, M. I.; Medved', T. Y.; Polikarpov, Y. M.; Yudina, K. S. Synthesis of Diphenylvinylphosphine Oxide. Russ. Chem. Bull. 1961, 10, 1891–1893. DOI: https://doi.org/10.1007/BF01184729.
  • Rabinowitz, R.; Pellon, J. Phosphorus-Containing Monomers. I. The Synthesis of Vinyl Phosphines, Oxides, Sulfides, and Phosphonium Compounds. J. Org. Chem. 1961, 26, 4623–4626. DOI: https://doi.org/10.1021/jo01069a101.
  • 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.
  • Baulin, V. E.; Evreinov, V. I.; Vostroknutova, Z. N.; Bondarenko, N. A.; Syundyukova, V. Kh.; Tsvetkov, E. N. Phosphorus-Containing Podands. IX. Synthesis of Oligoethylene Glycol Bis(Diphenylphosphinylethyl) Esters and Their Complexing Properties with Respect to Alkali Metal Cations in a Low-Polarity Solvent. Russ. Chem. Bull. 1992, 41, 914–918. DOI: https://doi.org/10.1007/BF00864538.
  • Bondarenko, N. A. Synthesis of Organophosphorus Complex-Forming Agents and Biologically Active Substances on the Basis of PH Acids. Russ. J. Gen. Chem. 1999, 69, 1016–1037, Chapter 2.2. p. 1025. DOI: https://doi.org/10.1002/chin.200017280.
  • Collins, D. J.; Mollard, S.; Rose, N.; Swan, J. M. Organophosphorus Compounds. XVI. 2-(N-Dialkylamino) Alkyldiphenylphosphines, Phosphine Oxides and Sulphides as Analogues of Methadone. Aust. J. Chem. 1974, 27, 2365–2372. DOI: https://doi.org/10.1071/CH9742365.
  • Märkl, G.; Merkl, B. Optisch Aktive β-(Amino)Ethyl-Phosphonsäureester, β-(Amino)-Ethylphenylphosphinsäureester, β-(Amino)Ethyl-Diphenylphosphinoxide Und β-(Amino) Ethyldiphenylphosphine. Tetrahedron Lett. 1981, 22, 4459–4462. DOI: https://doi.org/10.1016/S0040-4039(01)93014-X.
  • Maj, A. M.; Pietrusiewicz, K. M.; Suisse, I.; Agbossou, F.; Mortreux, A. Chiral β-Aminophosphine Oxides as Ligands for Ruthenium Assisted Enantioselective Transfer Hydrogenation of Ketones. Tetrahedron: Asymmetry 1999, 10, 831–835. DOI: https://doi.org/10.1016/S0957-4166(99)00063-4.
  • Matveeva, E. V.; Petrovskii, P. V.; Klemenkova, Z. S.; Bondarenko, N. A.; Odinets, I. L. A Practical and Efficient Green Synthesis of β-Aminophosphoryl Compounds via the Aza-Michael Reaction in Water. Compt. Rend. Chim. 2010, 13, 964–970. DOI: https://doi.org/10.1016/j.crci.2010.03.005.
  • Pietrusiewicz, K. M.; Zabłocka, M. Optically Active Phosphine Oxides. 4. A Straightforward Synthesis of P-Chiral 1,2-Diphosphinoylethanes. Tetrahedron Lett. 1988, 29, 1987–1990. DOI: https://doi.org/10.1016/S0040-4039(00)82097-3.
  • Bondarenko, N. A.; Bozhko, O. K.; Tsvetkov, E. N. Synthesis of Asymmetric P,P-Dialkyl-P’P’-Diphenylethylenediphosphine Dioxides. Russ. Chem. Bull. 1995, 44, 134–136. DOI: https://doi.org/10.1007/BF00696974.
  • Maj, A. M.; Pietrusiewicz, K. M.; Suisse, I.; Agbossou, F.; Mortreux, A. P-Chiral β-Aminophosphine Oxides vs. β-Aminophosphines as Auxiliaries for Ruthenium Catalysed Enantioselective Transfer Hydrogenation of Arylketones. J. Org. Chem. 2001, 626, 157–160. DOI: https://doi.org/10.1016/S0022-328X(01)00678-7.
  • Terekhova, M. I.; Kron, T. E.; Bondarenko, N. A.; Petrov, É. S.; Tsvetkov, E. N. Complexes of PdCl2 with Phosphoryl- and Thiophosphoryl Substituted Phosphines as Catalysts for the Hydrocarboxylation of Olefines. Russ. Chem. Bull. 1992, 41, 1555–1558. DOI: https://doi.org/10.1007/BF00863571.
  • Bondarenko, N. A. Synthesis of Organophosphorus Complex-Forming Agents and Biologically Active Substances on the Basis of PH Acids. Russ. J. Gen. Chem. 1999, 69, 1016–1037.Ref. [5], Chapter 2.3.2. p. 1029.
  • Turanov, A. N.; Karandashev, V. K.; Bondarenko, N. A. Extractive and Sorption Preconcentration of Rhenium (VII) Ions with the Use of Bis(Diphenylphosphoryl) Substituted Azapodand. Russ. J. Inorg. Chem. 2013, 58, 590–595. DOI: https://doi.org/10.1134/S0036023613050239.
  • Turanov, A. N.; Karandashev, V. K.; Artyushin, O. I.; Peregudov, A. S.; Khvostikov, V. A.; Bondarenko, N. A. Extraction Properties of Diphenyl{[N-(2-Diphenyl-Phosphenylethyl)-N-Alkyl]Carbamoylmethyl} Phosphine Oxides in Nitric Acid Solutions. Russ. J. Inorg. Chem. 2020, 65, 905–913. DOI: https://doi.org/10.31857/S0044457X20060240.
  • Bondarenko, N. A.; Rudomino, M. V.; Tsvetkov, E. N. β-Hydroxy- and β-Ethoxyethyldiphenylphosphine Oxides as Equivalents of Vinyldiphenylphosphine Oxide in Addition Reactions. Russ. Chem. Bull. 1990, 39, 1989–1989. DOI: https://doi.org/10.1007/BF00958287.
  • Tsvetkov, E. N.; Bondarenko, N. A.; Malakhova, I. G.; Kabachnik, M. I. A Simple Synthesis and Some Application of Substituted Phosphide and Phosphinite Anions. Synthesis 1986, 1986, 198–208. DOI: https://doi.org/10.1055/s-1986-31510.
  • Bondarenko, N. A.; Tsvetkov, E. N. Synthesis of Diphenylvinyphosphine Oxide from Diphenylphosphinous Acid. Zh. Obshch. Khim 1989, 59, 1533–1553.
  • Osipenko, N. G.; Tsvetkov, E. N. The Formation of Tetraalkylethylenediphosphine Dioxides in the Reaction of Potassium Dialkylphosphinites with Alkyl-2-Chloroethyl Esters. Zh. Obshch. Khim 1977, 47, 2620–2621.
  • Kharitonov, A. V.; Antoshin, A. E.; Tsvetkov, E. N. The Tetrahydrofuran Cycle Cleavage during the Interaction of 2-Chloromethyltetrahydrofuran with the Diphenylphosphinite Anion. Zh. Obshch. Khim 1987, 57, 2395–2396.
  • Bondarenko, N. A. Synthesis of Organophosphorus Complex-Forming Agents and Biologically Active Substances on the Basis of PH Acids. Russ. J. Gen. Chem. 1999, 69, 1016–1037. Chapter 3.2. p. 1032.
  • Evreinov, V. I.; Baulin, V. E.; Vostroknutova, Z. N.; Tsvetkov, E. N. Phosphorus-Containing Podands. 10. An Improved Method for Synthesis Oligoethylene Glycol Bis[2-(Diphenylphosphinoyl)Ethyl] Ethers and Their Complex-Forming Properties with Respect to Alkali Metal Cations in Anhydrous Acetonitrile. Russ. Chem. Bull. 1993, 42, 472–477. DOI: https://doi.org/10.1007/BF00698434.
  • Turanov, A. N.; Karandashev, V. K.; Bondarenko, N. A.; Urinovich, E. M.; Tsvetkov, E. N. Extraction Properties of Phosphoryl-Containing Azapodand in Hydrochloric Acid Media. Russ. J. Inorg. Chem. 1996, 41, 1658–1662.
  • Horner, L.; Lindel, H. Phosphororganische Verbindungen 1121 Reaktivität Und Selektivität Von Vinylphosphoniumsalzen Und Vinylphosphinoxiden Gegenüber Nucleophilen. Phosphorus Sulfur Silicon Relat. Elem. 1984, 20, 161–164. DOI: https://doi.org/10.1080/03086648408077624.
  • Postle, S. R.; Whitham, G. H. The Chemistry of Vinylphosphine Chalcogenides. Part 2.l. Some Nucleophilic and Electrophilic Additions. J. Chem. Soc. Perkin Trans. 1 1977, 2084–2088. DOI: https://doi.org/10.1039/p19770002084.
  • Campbell, I. G. M.; Stevens, I. D. R. Duality in Chemical Character of Secondary Phosphine Oxides. Chem. Commun. 1966, 15, 505–506. DOI: https://doi.org/10.1039/C19660000505.
  • Gordon, A. J.; Ford, R. A. The Chemist's Companion: A Handbook of Practical Data, Techniques, and References. Wiley: New York, 1972.
  • Bondarenko, N. A.; Kharlamov, A. V.; Vendilo, A. G. Synthesis of Nonsymmetrical Dialkylamines Based on Diphenylphosphinic Amides. Russ. Chem. Bull. 2009, 58, 1872–1885. DOI: https://doi.org/10.1007/s11172-009-0256-3.
  • Bondarenko, N. A. Synthesis of Organophosphorus Complex-Forming Agents and Biologically Active Substances on the Basis of PH Acids. Russ. J. Gen. Chem. 1999, 69, 1016–1037, Chapter 2.1. p. 1024.
  • Földeák, S.; Czombos, J.; Matkovics, B.; Pórszász, J. Synthesis of Substances Effecting on C.N.S. IV* Synthesis and Pharmacological Examination of Some Aminoethers. Acta Phys. Chem. Szeged 1963, 9, 134–142.
  • Shutt, J. R.; Trippett, S. Some Reactions of Vinylphosphonium Salts. J. Chem. Soc. C 1969, 2038–2043. DOI: https://doi.org/10.1039/j39690002038.

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