Abstract
Primary intermediates of P(III) chlorides reaction with aldehydes have been converted into the corresponding phosphates by treating with oxidants: dimethylsulfoxide and tert-butyl hypochlorite. In reactions of the intermediates with chlorinating agents (PCl5 and Cl2) the oxidation products are formed (due to the ligand exchange at quasiphosphonium center) along with the expected P(IV) acid chlorides.
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Gazizov, M.B., Khairullin, R.A., and Karimova, R.F., Russ. J. Gen. Chem., 2013, vol. 83, no. 12, p. 2293.
Gazizov, M.B., Khairullin, R.A., and Karimova, R.F., Russ. J. Gen. Chem., 2013, vol. 83, no. 12, p. 2281.
Plumb, J.B. and Griffin, C.E., J. Org. Chem., 1963, vol. 28, no. 10, p. 2908.
Cadogan, J.G., Cameron-Wood, M., and Foster, W.R., J. Chem. Soc., 1963, p. 2549.
Floyd, M.B. and Boozer, C.E., J. Am. Chem. Soc., 1963, vol. 85, no. 7, p. 984.
Bentrude, W.G., Tetrahedron Lett., 1965, no. 40, p. 3543.
Smirnov, A.N. and Khardin, A.P., Zh. Obshch. Khim., 1969, vol. 39, no. 9, p. 2138.
Corbridge, D.E.C., Phosphorus: An Outline of Its Chemistry, Biochemistry, and Technology, Amsterdam: Elsevier, 5th ed.: 1980.
Horner, L., Schalfer, H., and Ludwig, W., Chem. Ber., 1958, vol. 91, no. 1, p. 75.
Thompson, Q.E., J. Am. Chem. Soc., 1961, vol. 83, no. 4, p. 845.
Horner, L. and Jurgens, E., Chem. Ber., 1957, vol. 90, no. 10, p. 2184.
Walling, C. and Rabinowitz, R., J. Am. Chem. Soc., 1959, vol. 81, no. 5, p. 1243.
Walling, C., Busedow, O.H., and Savas, E.S., J. Am. Chem. Soc., 1960, vol. 82, no. 9, p. 2181.
Denney, D.B. and Gough, S.I., J. Am. Chem. Soc., 1965, vol. 87, no. 1, p. 138.
Denney, D.B., Relles, H.N., and Tsolis A.K., J. Am. Chem. Soc., 1964, vol. 86, no. 20, p. 4487.
Denney, D.B. and Relles, H.M., J. Am. Chem. Soc., 1964, vol. 86, no. 18, p. 3897.
Kirby, A.J. and Warren, S.G., The Organic Chemistry of Phosphorus, London: Elsevier, 1967.
Ochiai, E., J. Org. Chem., 1953, vol. 18, p. 534.
Olszewski W.F. and Howard, E., J. Am. Chem. Soc., 1958, vol. 81, no. 6, p. 1483.
Amonoo-Neizer, E.N., Pay, S.K., and Shaw, R.A., J. Chem. Soc., 1965, vol. 87, p. 4296.
Ruveda, M.A., Zerba, E.N., and Moutier Alda, E.M., Tetrahedron, 1973, vol. 29, no. 23, p. 585.
Petrov, K.A. and Sokol’skii, F.A., Zh. Obshch. Khim., 1956, vol. 26, no. 12, p. 3377.
Denney, D.B. and Lione, R.R., J. Am. Chem. Soc., 1962, vol. 84, no. 24, p. 4737.
Denney, D.B. and Hanifin, W., Tetrahedron Lett., 1963, no. 30, p. 2170.
Gazizov, T.Kh. and Pashinkin, A.P., Abstracts of Papers, Nauchnaya konf. IOFK im. A.E.Arbuzov, KFAN SSSR, Kazan, 1969, p. 4.
Lutsenko, I.F., Kraits, Z.S., and Proskurnina, M.V., Dokl. Akad. Nauk SSSR, 1963, vol. 148, no. 4, p. 846.
Kim, T.V., Ivanova, Zh. M., and Gololobov, Yu.G., Zh. Obshch. Khim., 1978, vol. 48, no. 2, p. 346.
Cloede, J., Mikolajezek, M., Lopusinski, A., and Omelanczuc, J., J. Pract. Chem., 1974, vol. 316, no. 4, p. 703.
Gazizov, M.B., Zakharov, V.M., Khairullin, R.A., and Moskva, V.V., Zh. Obshch. Khim., 1980, vol. 50, no. 7, p. 1510.
Timokhin, B.V., Kazantseva, M.V., and Donskikh, V.Yu., Zh. Obshch. Khim., 1989, vol. 59, no. 11, p. 2486.
Oroschnik, B.W. and Mallory, R.A., J. Am. Chem. Soc., 1950, vol. 72, no. 11, p. 4608.
Gazizov, M.B., Salakhutdinov, R.A., Zykova, T.V., and Sultanova, D.B., Zh. Obshch. Khim., 1978, vol. 48, no. 9, p. 1984.
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Original Russian Text © M.B. Gazizov, R.A. Khairullin, R.F. Karimova, 2014, published in Zhurnal Obshchei Khimii, 2014, Vol. 84, No. 1, pp. 79–85.
For communication II, see [1].
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Gazizov, M.B., Khairullin, R.A. & Karimova, R.F. Reaction of P(III) chlorides with aldehydes: III. Reaction of primary intermediates with oxidants and chlorinating agents. Russ J Gen Chem 84, 75–81 (2014). https://doi.org/10.1134/S1070363214010113
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DOI: https://doi.org/10.1134/S1070363214010113