The reactions of non-gem-hexanedioxytetrachlorocyclotriphosphazene with 2-(2-hydroxyethyl)thiophene, benzyl alcohol and 1,1,3,3-tetramethylguanidine. Spectroscopic studies of the derived products

References

• Gleria, M.; DeJaeger, R. (Eds.). Phosphazenes: A Worldwide Insight, New York, NY: Nova Science, 2004; 1048.
   Google Scholar
• Allcock, H. R.; Mark, H. F.; Bikales, N. M.; Overberger, C. G.; Menges, G.; Kroschwitz, J. I. (Eds.), Encyclopedia of Polymer Science and Engineering, New York, NY: John Wiley & Sons, 1988, 13, 31.
   Google Scholar
• Allen, C. W. Inorganic and Organometallic Polymers and Materials. J. Inorg. Organomet. Polym. Mater. 2007, 17, 341–348. DOI: 10.1007/s10904-007-9132-5.
   Web of Science ®Google Scholar
• Allen, C. W.; Hernandez-Rubio, D.; Gleria, M.; DeJaeger, R. (Eds.), Phosphazenes: A Worldwide Insight, New York, NY: Nova Science, 2004, 20, 485–503. DOI: 10.1177/073490419301100404.
   Google Scholar
• Inoue, K.; Yamauchi, T.; Itoh, T.; Ihara, E. Ionic Conductivity of Cross-linked Polymethacrylate Derivatives/Cyclophosphazenes/Li+. Salt Complexes. J. Inorg. Organomet. Polym. 2007, 17, 367–375. DOI: 10.1007/s10904-007-9126-3.
   Web of Science ®Google Scholar
• Barbera, J.; Bardaji, M.; Jimenez, J.; Laguna, A.; Martinez, M. P.; Oriol, L.; Serrano, J. L.; Zaragozano, I. Columnar Mesomorphic Organizations in Cyclotriphosphazenes. J. Am. Chem. Soc. 2005, 127, 8994–9002. DOI: 10.1021/ja051042w.
   PubMed Web of Science ®Google Scholar
• İlter, E.; Asmafiliz, N.; Kılıç, Z.; Açık, L.; Yavuz, M.; Bali, E. B.; Solak, A. O.; Buyükkaya, F.; Dal, H.; Hökelek, T. Syntheses, Structural and Electrochemical Investigations, Biological Activities and DNA Interactions of New Spirocyclic Monoferrocenylcyclotriphosphazenes. Polyhedron. 2010, 29, 2933–2944. DOI: 10.1016/j.poly.2010.07.017.
   Web of Science ®Google Scholar
• Görgülü, A. O.; Koran, K.; Özen, F.; Tekin, S.; Sandal, S. Synthesis, structural Characterization and Anti-carcinogenic Activity of New Cyclotriphosphazenes Containing Dioxybiphenyl and Chalcone Groups. J. Mol. Struct. 2015, 1087, 1–10. DOI: 10.1016/j.molstruc.2015.01.033.
   Web of Science ®Google Scholar
• Shaw, R. A. The Reactions of Phosphazenes with Difunctional and Polyfunctional Nucleophilic Reagents. Phosphorus Sulfur Silicon Relat. Elem. 1989, 45, 103–136. DOI: 10.1080/10426508908046081.
   Web of Science ®Google Scholar
• Guerch, G.; Labarre, J. F.; Lahana, R.; Roques, R.; Sournies, F. J. An Answer to the Spiro Versus Ansa Dilemma in Cyclophosphazenes. Mol. Struct. 1983, 99, 275–282. DOI: 10.1016/0022-2860(83)90030-3.
   Web of Science ®Google Scholar
• Castera, P.; Faucher, J. P.; Guerch, G.; Lahana, R.; Mahmoun, A.; Sournies, F.; Labarre, J. F. An Answer to the SPIRO Versus ANSA Dilemma in Cyclophosphazenes. Part VII. Neither SPIRO nor ANSA: The BINO Dicyclotriphosphazenes, N3P3Cl5-[HN-(CH2)n-NH]Cl5P3N3. Inorg. Chim. Acta. 1985, 108, 29–33. DOI: 10.1016/S0020-1693(00)84319-4.
   Web of Science ®Google Scholar
• Silah, H.; Ture, S. Synthesis and the Structural Characterization of Single-, Double- and Triple-bridged Derivatives of Cyclochlorophosphazene with Bis(2-Hydroxyethyl) Ether and 2,2-dimethylpropane-1,3-Diol. Phosphorus Sulfur Silicon Relat. Elem. 2014, 189, 198–214. DOI: 10.1080/10426507.2013.807255.
   Web of Science ®Google Scholar
• Yıldırım, T.; Bilgin, K.; Çiftçi, G. Y.; Eçik, E. T.; Şenkuytu, E.; Uludağ, Y.; Tomak, L.; Kılıç, A. Synthesis, Cytotoxicity and Apoptosis of Cyclotriphosphazene Compounds as anti-cancer Agents. Eur. J. Med. Chem. 2012, 52, 213–220. DOI: 10.1016/j.ejmech.2012.03.018.
   PubMed Web of Science ®Google Scholar
• Coles, S. J.; Davies, D. B.; Eaton, R. J.; Hursthouse, M. B.; Kılıç, A.; Mayer, T. A.; Shaw, R. A.; Çiftçi, G. Y. Chiral Configurations of Spermine-bridged Cyclotriphosphazatrienes. J. Chem. Soc., Dalton Trans. 2002, 3, 365–370. DOI: 10.1039/b104973a.
   Google Scholar
• Beşli, S.; Coles, S. J.; Davies, D. B.; Eaton, R. J.; Hursthouse, M. B.; Kılıç, A.; Shaw, R. A.; Çiftçi, G. Y.; Yeşilot, S. Anomalous NMR Behavior of Meso Compounds with Remote Stereogenic Centers on Addition of Chiral Shift Reagent or Chiral Solvating Agent. J. Am. Chem. Soc. 2003, 125, 4943–4950. DOI: 10.1021/ja028871r.
   PubMed Web of Science ®Google Scholar
• Alkubaisi, A. H.; Parkes, H. G.; Shaw, R. A. The Reactions of Hexachlorocyclotriphosphazatriene with Ethane-, 1,3-Propane- and 1,4-Butane-diols. Spiro, Ansa, Bridged and Dangling Derivatives and Their 31P and 1H Nuclear Magnetic Resonance Spectra. Heterocycles. 1989, 28, 347–358. DOI: 10.3987/COM-88-S17.
   Web of Science ®Google Scholar
• Castera, P.; Faucher, J. P.; Grainer, M.; Labarre, J. F. The Dispiro N3P3Cl2 [HN-(CH2)3,4-NH]2 and Trispiro N3P3[HN-(CH2)3-NH]3 Derivatives. Phosphorus Sulfur Silicon Relat. Elem. 1987, 32, 37–42. DOI: 10.1016/0022-2860(84)87244-0.
   Web of Science ®Google Scholar
• Muralidhara, M. G.; Grover, N.; Chandrasekhar, V. Reactions of 1,3-butanediol with Hexachlorocyclotriphosphazene: Unusual Non-equivalence of Phosphorus Nuclei in the Spirocyclic Product N3P3Cl4[OCH(CH3)CH2CH2O]. Polyhedron. 1993, 12, 1509–1513. DOI: 10.1016/S0277-5387(00)84591-X.
   Web of Science ®Google Scholar
• Allcock, H. R.; Turner, M. L.; Visscher, K. B. Synthesis of Transannular- and Spiro-substituted Cyclotriphosphazenes: X-ray Crystal Structures of 1,1-[N3P3(OCH2CF3)4{O2C12H8}], 1,3-[N3P3(OCH2CF3)4{O2C12H8}], 1,1-[N3P3(OCH2CF3)4 {O2C10H6}], and 1,3-[N3P3(OCH2CF3)4}O2C10H6}]. Inorg. Chem. 1992, 31, 4354–4364. DOI: 10.1021/ic00047a024.
   Web of Science ®Google Scholar
• Allcock, H. R.; Diefenbach, U.; Pucher, S. R. New Mono- and Trispirocyclotriphosphazenes from the Reaction of (NPCl2)3 with Aromatic Ortho Dinucleophiles. Inorg. Chem. 1994, 33, 3091–3095. DOI: 10.1021/ic00092a013.
   Web of Science ®Google Scholar
• Brandt, K.; Kupka, T.; Drodz, J.; van de Grampel, J. C.; Meetsma, A.; Jekel, A. P. New Dioxytetraethyleneoxy Macrocyclic Cyclophosphazene Derivatives. Inorg. Chim. Acta 1995, 228, 187–192. DOI: 10.1016/0020-1693(94)04162-O.
   Web of Science ®Google Scholar
• Brandt, K.; Porwolik-Czomperlik, I.; Siwy, M.; Kupka, T.; Shaw, R. A.; Davies, D. B.; Hursthouse, M. B.; Sykara, G. D. Thermodynamic vs Supramolecular Effects in the Regiocontrol of the Formation of New Cyclotriphosphazene-Containing Chiral Ligands with 1,1-Binaphthyl Units: Spiro vs Ansa Substitution at the N3P3 Ring. J. Am. Chem. Soc. 1997, 119, 12432–12440. DOI: 10.1021/ja972372m.
   Web of Science ®Google Scholar
• Brandt, K.; Porwolik-Czomperlik, I.; Siwy, M.; Kupka, T.; Shaw, R. A.; Ture, S.; Clayton, A.; Davies, D. B.; Hursthouse, M. B.; Sykara, G. D. A Regioselective Route to New Polytopic Receptors by Diaminolysis of Chlorocyclotriphosphazatriene-Containing Crown Ethers. J. Org. Chem. 1999, 64, 7299–7304. DOI: 10.1021/jo990489i.
   Web of Science ®Google Scholar
• Davies, D. B.; Clayton, T. A.; Eaton, R. J.; Shaw, R. A.; Egan, A.; Hursthouse, M. B.; Sykara, G. D.; Porwolik-Czomperlik, I.; Siwy, M.; Brandt, K. Chiral Configurations of Cyclophosphazenes. J. Am. Chem. Soc. 2000, 122, 12447–12457. DOI: 10.1021/ja0028469.
   Web of Science ®Google Scholar
• Muralidharan, K.; Venugopalan, P.; Elias, A. J. Ansa versus Spiro Substitution of Cyclophosphazenes: Is Fluorination Essential for Ansa to Spiro Transformation of Cyclophosphazenes: Fluorination Essential for Ansa to Spiro Transformation of Cyclophosphazenes? Inorg. Chem. 2003, 42, 3176–3182. DOI: 10.1021/ic034119v.
   PubMed Web of Science ®Google Scholar
• Beşli, S.; Coles, S. J.; Davies, D. B.; Eaton, R. J.; Hursthouse, M. B.; Kılıç, A.; Shaw, R. A. Structural and Stereogenic Properties of Spiro- and Ansa-substituted 1,3-propanedioxy Derivatives of a Spermine-bridged Cyclotriphosphazene. Polyhedron 2006, 25, 953–962. DOI: 10.1016/j.poly.2005.10.023.
   Web of Science ®Google Scholar
• Beşli, S.; Coles, S. J.; Davarcı, D.; Davies, D. B.; Hursthouse, M. B.; Kılıç, A. Formation of Spiro and Ansa Derivatives in the Reaction of 2,2,3,3,4,4- hexafluoropentane-1,5-diol with Cyclotriphosphazene: Comparison with 2,2,3,3-Tetrafluorobutane-1,4-Diol. Polyhedron 2007, 26, 5283–5292. DOI: 10.1016/j.poly.2007.07.050.
   Web of Science ®Google Scholar
• Beşli, S.; Coles, S. J.; Davies, D. B.; Erkovan, A. O.; Hursthouse, M. B.; Kılıç, A. Single-, Double- and Triple-bridged Derivatives of Cyclotriphosphazenes with an Octafluorohexane-1,6-Diol. Polyhedron. 2009, 28, 3593–3599. DOI: 10.1016/j.poly.2009.07.042.
   Web of Science ®Google Scholar
• Beşli, S.; Coles, S. J.; Davies, D. B.; Eaton, R. J.; Hurtshouse, M. B.; Kılıç, A.; Shaw, R. A. Crystallographic Proof of Double Walden Inversion in Nucleophilic Substitution Reactions of Macrocyclic-Cyclotriphosphazene Derivatives. Eur. J. Inorg. Chem. 2005, 5, 959–966. DOI: 10.1002/ejic.200400745.
   Web of Science ®Google Scholar
• Beşli, S.; Coles, S. J.; Davies, D. B.; Hursthouse, M. B.; Kılıç, A.; Shaw, R. A. A Spiro to Ansa Rearrangement in Cyclotriphosphazene Derivatives. Dalton Trans. 2007, 2792–2801. DOI: 10.1039/B703541A.
   PubMed Web of Science ®Google Scholar
• Davarcı, D.; Beşli, S.; Yüksel, F. Reactions of Cyclotriphosphazene with 1,6-diaminohexane and 1,8-diaminooctane: Mono-ansa, Double and Triple-bridged Derivatives. Polyhedron. 2014, 68, 10–16. DOI: 10.1016/j.poly.2013.10.012.
   Web of Science ®Google Scholar
• Beşli, S.; Coles, S. J.; Davarcı, D.; Davies, D. B.; Yuksel, F. Effect of Chain Length on the Formation of Intramolecular and Intermolecular Products: Reaction of Diols with Cyclotriphosphazene. Polyhedron. 2011, 30, 329–339. DOI: 10.1016/j.poly.2010.10.020.
   Web of Science ®Google Scholar
• Al-Madfa, H. A.; Shaw, R. A.; Ture, S. The Reactions of Hexachlorocyclotriphosphazatriene with 2, 2-dimethylpropane-1, 3-diol. Nuclear Magnetic Resonance Studies of the Products. Phosphorus Sulfur Silicon Relat. Elem. 1990, 53, 333–338. DOI: 10.1080/10426509008038043.
   Web of Science ®Google Scholar
• Shaw, R. A.; Fitzsimmons, B. W.; Smith, B. C. The Phosphazenes (phosphonitrilic Coinpounds). Chem. Rev. 1962, 62, 247–281. DOI: 10.1021/cr60217a004.
   Web of Science ®Google Scholar
• Dell, D.; Fitzsimmons, B. W.; Shaw, R. A. Chemistry of Cyclophosphazenes. J. Chem. Soc. 1965, 4070–4073. DOI: 10.1039/JR9650004070.
   Web of Science ®Google Scholar
• Carroll, A. P.; Shaw, R. A. Phosphorus–Nitrogen Compounds. Part XXI. Alkylthio- and Phenylthio-Cyclotriphosphazatrienes. J. Chem. Soc. 1966, 914–921. DOI: 10.1039/J19660000914.
   Web of Science ®Google Scholar
• Shaw, R. A. The Reactions of Halogenocyclophosphazenes with Nitrogenous Base. Z. Naturforsch. 1976, 31b, 641–667. DOI: B/31/ZNB-1976-31b-064.
   Google Scholar
• Das, R. N.; Shaw, R. A.; Smith, B. C.; Woods, M. The Reactions of Hexachlorocyclotriphosphazatriene with Ethylamine: Comparisons with Isopropylamine and t-Butylamine. J. Chem. Soc., Dalton Trans. 1973, 709–715. DOI: 10.1039/DT9730000709.
   Google Scholar
• Das, S. K.; Keat, R.; Shaw, R. A.; Smith, B. C. The Reactions of Hexachlorocyclotriphosphazatriene with t-Butylamine. J. Chem. Soc. 1965, 0, 5032–5036. DOI: 10.1039/JR9650005032.
   Web of Science ®Google Scholar
• Lingley, D. J.; Shaw, R. A.; Yu, H. S. Solvent Effects in the Reactions of N3P3Cl6 with Secondary Amines. Inorg. Nucl. Chem. Lett. 1980, 16, 219–221. DOI: 10.1016/0020-1650(80)80125-5.
   Web of Science ®Google Scholar
• Fincham, J. K.; Hursthouse, M. B.; Parkes, H. G.; Shaw (née Gözen), L. S.; Shaw, R. A. The Structures of N3P3(NH2)2Cl4, N3P3(NPPh3)(NH2)Cl4 and N3P3(NPPh3)Cl5 and a Comparison with Other Phosphazenylphosphazenes. The Relationship of Conformation in the Solid State to Conformation in Solution. Acta Crystallogr. B Struct. Sci. 1986, B42, 462–4762. DOI: 10.1107/S0108768186097872.
   Web of Science ®Google Scholar
• Schmutz, J. L.; Allcock, H. R. Reaction of Sodium 2,2,2-trifluoroethoxide with Hexachlorocyclotriphosphazene. Inorg. Chem. 1975, 14, 2433–2438. DOI: 10.1021/ic50152a027.
   Web of Science ®Google Scholar
• Ture, S. Phosphorus-Nitrogen Compounds: Reinvestigation of the Reactions of Hexachlorocyclotriphosphazene with 1,4-Butane- and 1,6-Hexane-Diols—NMR Studies of the Products. Phosphorus. Sulfur Silicon Relat. Elem. 2016, 191, 1174–1182. DOI: 10.1080/10426507.2016.1160238.
   Web of Science ®Google Scholar
• M, K. Valence‐Bond Interpretation of Electron‐Coupled Nuclear Spin Interactions; Application to Methane. J. Chem. Phys. 1959, 30, 11–15. DOI: 10.1063/1.1729943.
   Web of Science ®Google Scholar
• Karplus, M. Vicinal Proton Coupling in Nuclear Magnetic Resonance. J. Am. Chem. Soc. 1963, 85, 2870–2871. DOI: 10.1021/ja00901a059.
   Web of Science ®Google Scholar
• Musher, J. I.; Corey, E. J. Virtual Long-range Spin-spin Couplings in NMR. Tetrahedron. 1962, 18, 791–809. DOI: 10.1016/S0040-4020(01)92729-2.
   Web of Science ®Google Scholar