Journal of Organometallic Chemistry p. 275 - 282 (1985)
Update date:2022-08-02
Topics:
Chojnowski, J.
Cypryk, M.
Michalski J.
Wozniak, L.
In order to throw light on the possible role of positively charged tetra-coordinate silicon intermediates in the racemization of α-NpPhMeSiCl (1) induced by uncharged nucleophiles two sets of kinetic studies have been carried out.In the first the rates of two reactions namely racemization of 1 catalysed by (PhO)2(Me3SiO)P=O (2) and transsilylation of 2 with 1, which take place together and are believed to involve the same intermediate were determined; the transsilylation was found to be faster than the racemization, and involved transient formation of an optically active product.In the second the racemization of 1 catalysed by HMPT in various CCl4/CH2Cl2 mixtures was studied; the rate was found to increase markedly with increase in the dielectric constant of the medium.The results of both sets of experiments were consistent with a mechanism involving a silyloxyphosphonium cation intermediate.
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Doi:10.1016/S0040-4039(00)98967-6
(1985)Doi:10.1021/ja00261a022
(1986)Doi:10.1039/c39850000793
(1985)Doi:10.1016/0304-5102(87)80095-0
(1987)Doi:10.1021/jo00350a095
(1985)Doi:10.1016/S0040-4039(00)94847-0
(1985)