Abstract
The survey summarizes modern methods of synthesis and reactivity of tetracoordinated phosphorus cage compounds containing one or more endocyclic P–C bonds (phosphine oxides, phosphinates and phosphonates, phosphatripticenes and others). Intramolecular cyclization reactions including electrophilic aromatic substitution with unsaturated organophosphorus compounds, reactions of P–H-derivatives with carbonyl compounds as well as cycloaddition reactions involving I–IV-coordinated phosphorus derivatives are considered.
Similar content being viewed by others
References
Corbridge, D.E.C., Phosphorus: Chemistry, Biochemistry and Technology, Boca Raton; New York; London CRC Press, Taylor & Francis Group, 2013.
Almstätter, S., Eberl, M., Balázs, G., Bodensteiner, M., and Scheer, M., Z. Anorg. Allg. Chem., 2012, vol. 638, no. 11, p. 1739. doi 10.1002/zaac.201200116
Nifant’ev, E.E., Predvoditelev, D.A., Strebkova, E.V., and Malenkovskaya, M.A., Doklady Chem., 2007, vol. 416, no. 1, p. 220. doi 10.1134/S0012500807090054
Regitz, M., Hoffrnann, A., and Bergsträßer, U., in Modern Acetylene Chemistry, Stang, P.J. and Diederich, F., Eds., Weinheim; New York; Basel; Cambridge; Tokyo: VCH, 1995, p. 173.
Mason, M.R., J. Cluster Sci., 1998, vol. 9, no. 1, p. 1. doi 10.1023/A:1022671821691
Venkataramu, S.D., Macdonell, G.D., Purdum, W.R., El-Deek, M., and Berlin, K.D., Chem. Rev., 1977, vol. 77, no. 2, p. 121. doi 10.1021/cr60306a001
Gage, J.C., Brit. J. Ind. Med., 1970, vol. 27, no. 1, p. 1.
Bellet, E.M. and Casida, J.E., Science, 1973, vol. 182, no. 4117, p. 1135. doi 10.1126/science.182.4117.1135
Bowery, N.G., Collins, J.F., and Hill, R.G., Nature, 1976, vol. 261, no. 5561, p. 601. doi 10.1038/261601a0
Martynov, I.V., Fetisov, V.I., and Sokolov, V.B., Itogi Nauki i Tekhniki, Ser. Org. Khim., 1989, vol. 11, p. 3.
Pringle, P.G. and Smith, M.B., in Phosphorus(III) Ligands in Homogeneous Catalysis: Design and Synthesis, Kamer, P.C.J. and van Leeuwen, P.W.N.M., Eds., New York: John Wiley, 2012, ch. 13, p. 391. doi 10.1002/9781118299715.ch13
Weymiens, W., Slootweg, J.C., and Lammertsma, K., in Phosphorus Compounds: Advanced Tools in Catalysis and Material Sciences (Catalysis by Metal Complexes), Peruzzini, M. and Gonsalvi, L., Eds., Dodrecht; Heidelberg; London; New York: Springer, 2011, vol. 37, ch. 2, p. 21. doi 10.1007/978-90-481-3817-3_2
Vysotskii, V.I., Chuprakova, K.G., and Tilichenko, M.N., J. Gen. Chem. USSR. Engl. Transl., 1976, vol. 46, no. 4, p. 783.
Hanaya, T., Fujii, Y., and Yamamoto, H., J. Chem. Res.(S), 1998, no. 12, p. 790. doi 10.1039/A804961K
Dessinges, A. and Vasella, A., Carbohydr. Res., 1988, vol. 174, p. 47. doi 10.1016/0008-6215(88)85080-8
Kobayashi, J., Goto, K., and Kawashima, T., J. Am. Chem. Soc., 2001, vol. 123, no. 14, p. 3387. doi 10.1021/ja0056264
Kobayashi, J., Goto, K., Kawashima, T., Schmidt, M.W., and Nagase, S., J. Am. Chem. Soc., 2002, vol. 124, no. 14, p. 3703. doi 10.1021/ja011458j
Nakafuji, S.-Y., Kobayashi, J., Kawashima, T., and Schmidt, M.W., Inorg. Chem., 2005, vol. 44, no. 19, p. 6500. doi 10.1021/ic050679d
Kobayashi, J. and Kawashima, T., Phosphorus, Sulfur, Silicon, Relat. Elem., 2009, vol. 184, no. 4, p. 1028. doi 10.1080/10426500902748080
Kobayashi, J., Goto, K., and Kawashima, T., Phosphorus, Sulfur, Silicon, Relat. Elem., 2001, vol. 169, p. 273. doi 10.1080/10426500108546641
Kobayashi, J., Goto, K., and Kawashima, T., Phosphorus, Sulfur, Silicon, Relat. Elem., 2002, vol. 177, nos. 6–7, p. 1405. doi 10.1080/10426500212207
Kobayashi, J., Goto, K., Kawashima, T., Schmidt, M.W., and Nagase, S., Chem. Eur. J., 2006, vol. 12, no. 14, p. 3811. doi 10.1002/chem.200500864
Sadykova, Y.M., Dalmatova, N.V., Burilov, A.R., Pudovik, M.A., and Dobrynin, A.B., Russ. Chem. Bull., 2011, vol. 60, no. 10, p. 2078. doi 10.1007/s11172-011- 0317-2
Sadykova, Y.M., Knyazeva, I.R., Burilov, A.R., Pudovik, M.A., Dobrynin, A.B., Litvinov, I.A., and Sinyashin, O.G., Heteroatom Chem., 2011, vol. 22, no. 1, p. 1. doi 10.1002/hc.20646
Sadykova, Y.M., Dalmatova, N.V., Voronina, Y.K., Burilov, A.R., Pudovik, M.A., and Sinyashin, O.G., Heteroatom. Chem., 2012, vol. 23, no. 4, p. 340. doi 10.1002/hc.21022.
Kashman, Y. and Awerbouch, O., Tetrahedron, 1970, vol. 26, no. 17, p. 4213. doi 10.1016/S0040-4020(01)93063-7
Kashman, Y. and Awerbouch, O., Tetrahedron, 1975, vol. 31, no. 1, p. 33. doi 10.1016/0040-4020(75)80008-1
Quin, L.D., Caster, K.C., and Kisalus, J.C., J. Am. Chem. Soc., 1984, vol. 106, no 23, p. 7021. doi 10.1021/ja00335a027
Awerbouch, O. and Kashman, Y., Tetrahedron, 1975, vol. 31, no. 1, p. 45. doi 10.1016/0040-4020(75)80009-3
Awerbouch, O. and Kashman, Y., Tetrahedron, 1975, vol. 31, no. 1, p. 53. doi 10.1016/0040-4020(75)80010-X
Rudi, A. and Kashman, Y., Org. Magn. Res., 1977, vol. 10, no. 1, p. 245. doi 10.1002/mrc.1270100156
Gaumont, A.-C., Guillemin, J.-C., and Denis, J.-M., J. Chem. Soc. Chem. Commun., 1994, no. 8, p. 945. doi 10.1039/C39940000945
Zagidullin, A., Ganushevich, Y., Miluykov, V., Krivolapov, D., Kataeva, O., Sinyashin, O., and Hey-Hawkins, E., Org. Biomol. Chem., 2012, vol. 10, no. 27, p. 5298. doi 10.1039/c2ob25532d
Zagidullin, A., Ganushevich, Y., Miluykov, V., Sinyashin, O., and Hey-Hawkins, E., Phosphorus, Sulfur, Silicon, Relat. Elem., 2013, vol. 188, nos. 1–3, p. 238. doi 10.1080/10426507.2012.744017
Zagidullin, A., Miluykov, V., Sinyashin, O., Lonnecke, P., and Hey-Hawkins, E., Heteroatom Chem., 2014, vol. 25, no. 1, p. 28. doi 10.1002/hc.21132
Deschamps, E. and Mathey, F., J. Chem. Soc. Chem. Commun., 1984, no. 18, p. 1214. doi 10.1039/C39840001214
Quin, L.D., Hughes, A.N., Kisalus, J.C., and Pete, B., J. Org. Chem., 1988, vol. 53, no. 8, p. 1722. doi 10.1021/jo00243a023
Haque, M., Horne, W., Cremer, S.E., and Most, J.T., J. Chem. Soc. Perkin Trans. 2, 1981, no. 8, p. 1000. doi 10.1039/P29810001000
Quin, L.D. and Mesch, K.A., J. Chem. Soc. Chem. Commun., 1980, no. 20, p. 959. doi 10.1039/C39800000959
Mesch, K.A. and Quin, L.D., Tetrahedron Lett., 1980, vol. 21, no. 50, p. 4791. doi 10.1016/0040-4039(80) 80141-9
Quin, L.D., Kaster, K.S., and Kisalus, J.S., Phosphorus and Sulfur, 1983, vol. 18, no. 1–3, p. 105. doi 10.1080/03086648308075978
Dabritz, F., Theumer, G., Gruner, M., and Bauer, I., Tetrahedron, 2009, vol. 65, no. 15, p. 2995. doi 10.1016/j.tet.2009.01.102
Scott, L.T. and Cooney, M.J., Modern Acetylene Chemistry, Stang, P.J. and Diederich, F., Eds., Weinheim; New York; Basel; Cambridge; Tokyo: VCH, 1995, ch. 9, p. 321.
Kobayashi, J., Agou, T., and Kawashima, T., Chem. Lett., 2003, vol. 32, no. 12, p. 1144. doi 10.1246/cl.2003.1144
Kobayashi, J., Agou, T., and Kawashima, T., Phosphorus, Sulfur, Silicon, Relat. Elem., 2004, vol. 179, nos. 4–5, p. 959. doi 10.1080/10426500490429086
Agou, T., Kobayashi, J., and Kawashima, T., Heteroatom Chem., 2004, vol. 15, no. 6, p. 437. doi 10.1002/hc.20038
Uchiyama, Y., Sugimoto, J., Shibata, M., Yamamoto, G., and Mazaki, Y., Bull. Chem. Soc. Jap., 2009, vol. 82, no. 7, p. 819. doi 10.1246/bcsj.82.819
Ishii, A., Takaki, I., Nakayama, J., and Hoshino, M., Tetrahedron Lett., 1993, vol. 34, no. 51, p. 8255. doi 10.1016/S0040-4039(00)61404-1
Ishii, A., Tsuchiya, T., Nakayama, J., and Hoshino, M., Tetrahedron Lett., 1993, vol. 34, no. 14, p. 2347. doi 10.1016/S0040-4039(00)77610-6
Ishii, A., Yoshioka, R., Nakayama, J., and Hoshino, M., Tetrahedron Lett., 1993, vol. 34, no. 51, p. 8259. doi 10.1016/S0040-4039(00)61405-3
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © V.F. Mironov, G.A. Ivkova, L.M. Burnaeva, 2016, published in Zhurnal Obshchei Khimii, 2016, Vol. 86, No. 12, pp. 1987–1999.
Rights and permissions
About this article
Cite this article
Mironov, V.F., Ivkova, G.A. & Burnaeva, L.M. Tetracoordinate phosphorus cage compounds with endocyclic P–C bonds: Synthesis and reactivity. Russ J Gen Chem 86, 2624–2635 (2016). https://doi.org/10.1134/S1070363216120094
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363216120094