Abstract
Tribenzylphosphine oxide readily and stereoselectively reacts with aliphatic, aromatic, and heteroaromatic aldehydes in the presence of strong bases yielding exclusively (or predominantly) E-isomers of 1-organyl-2-phenylethenes and dibenzylphosphinic acid.
Similar content being viewed by others
REFERENCES
Horner, L., Hoffmann, H., Wippel, H.G., and Klahre, G., Chem. Ber., 1959, vol. 92, pp. 2499–2505.
Kabachnik, M.I., Medved', T.Ya., and Matrosov, E I., Dokl. Akad. Nauk SSSR, 1965, vol. 162, no. 2, pp. 339–342.
Buss, A.D., Greeves, N., Mason, R., and Warren, S., J. Chem. Soc., Perkin Trans. I, 1987, no. 12, pp. 2569–2577.
Buss, A.D. and Warren, S., J. Chem. Soc., Perkin Trans. I, 1985, no. 11, pp. 2307–2325.
Klayden, J. and Warren, S., Angew. Chem., 1996, vol. 108, no. 3, pp. 261–291.
Dombrovskii, A.V. and Dombrovskii, B.A., Usp. Khim., 1966, vol. 35, no. 10, pp. 1771–1787.
Vatsuro, K.V. and Mishchenko, G.L., Imennye reaktsii v organicheskoi khimii (Personal Reaction in Organic Chemistry), Moscow: Khimiya, 1976, p. 456.
Boutagy, J. and Thomas, R., Chem. Rev., 1974, vol. 74, no. 1, pp. 87–99.
Amstrong, D.R., Barr, D., Davidson, M.G., Hutton, G., O'Brien, P., Snaith, R., and Warren, S., J. Organometal. Chem., 1997, vol. 529, no. 1, pp. 29–33.
Buss, A.D. and Warren, S., Tetrahedron Lett., 1983, vol. 24, no. 36, pp. 3931–3935.
Cavalla, D., Cruse, W.B., and Warren, S., J. Chem. Soc., Perkin Trans. I, 1987, no. 9, pp. 1883–1898.
Gusarova, N.K., Ivanova, N.I., Reutskaya, A.M., Arbuzova, S.N., Trofimov, B.A., Zh. Org. Khim., 1999, vol. 69, no. 11, pp. 1922–1923.
Ivanova, N.I., Reutskaya, A.M., Arbuzova, S.N., Baikalova, L.V., Afonin, A.V., Gusarova, N.K., and Trofimov, B.A., Khim. Geterotsikl. Soed., 2000, no. 2, pp. 262–264.
Gusarova, N.K., Malysheva, S.F., Arbuzova, S.N., and Trofimov, B.A., Izv. RAN, Ser. Khim., 1998, no. 9, pp. 1695–1702.
Baikalova, L.V., Domnina, E.S., Chipanina, N.N., Afonin, A.V., and Shulunova, A.M., Izv. Russian Akad. Nauk, Ser. Khim., 1999, no. 5, pp. 971–975.
Trofimov, B.A., Mikhaleva, A.I., Vasil'tsov A.M., Schmidt, E.Yu., Tarasova, O.A., Morozova, L.V., Sobenina, L.N., Preiss, T., and Henkelmann, J., Synthesis, 2000, no. 8, pp. 1125–1132.
Purdela, D. and Vylchanu, R., Khimiya organicheskikh soedinenii fosfora (Chemistry of Phosphorus Organic Compounds), Moscow: Khimiya, 1972.
Erastov, O.A. and Nikonov, G.G., Funktsional'nozameshchennye fosfiny i ikh proizvodnye (Functionally Substituted Phosphines and Its Derivatives), Moscow: Mir, 1986, p. 238.
Horner, L., Klahre, G., Toscano, G., and Ertel, H., Chem. Ber., 1961, vol. 94, pp. 1987–1996.
Simeonov, A., Matsushita, M., Juban, E.A., Thompson, E.H.Z., Hoffman, T.Z., Beuscher, A.E., Taylor, M.J., Wirsching, P., Rettig, W., McCusker, J.K., Stevens, R.C., Millar, D.P., Schultz, P.G., Lerner, R.A., and Janda, K.D., Science, 2000, vol. 290, pp. 307–313.
Kudryavtseva, L.I. and Feshchenko, H.G., Zh. Obshch. Khim., 1981, vol. 51, no. 2, pp. 478–479; Kudryavtseva, L.I., Zh. Obshch. Khim., 1989, Obshch. Khim., vol. 59, no. 5, pp. 1027–1031.
Worm, A.T. and Brewster, J.H., J. Org. Chem., Obshch. Khim., 1970, vol. 35, no. 5, pp. 1715–1716.
Seyferth, D. and Singh, G., J. Am. Chem. Soc., 1965, Obshch. Khim., vol. 87, no. 18, pp. 4156–4162.
Seus, E.J. and Wilson, C.V., J. Org. Chem., 1961, Obshch. Khim., vol. 26, no. 12, p. 524.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Gusarova, N.K., Ivanova, N.I., Reutskaya, A.M. et al. Reaction of Tribenzylphosphine Oxide with Aldehydes. Russian Journal of Organic Chemistry 37, 1726–1730 (2001). https://doi.org/10.1023/A:1013974001957
Issue Date:
DOI: https://doi.org/10.1023/A:1013974001957