Journal of organometallic chemistry

Effects of the substituents Y in reactions of compounds of the type (Me3Si) 3CSiH (C6H4Y-p) I. Evidence against the SN2 (intermediate) mechanism for methanolysis …

DB Azarian, C Eaborn, PD Lickiss

Index: Azarian, Davoud B.; Eaborn, Colin; Lickiss, Paul D. Journal of Organometallic Chemistry, 1987 , vol. 330, p. 1 - 8

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Citation Number: 8

Abstract

Abstract The rates of methanolysis of the iodides TsiSiH (C 6 H 4 Yp) I (Y MeO, Me, H, Cl, or CF 3) in 1/1 v/v MeOH/dioxane have been shown to be increased by electron withdrawal by Y and correspondingly decreased by electron release. This is taken to imply that the methanol is covalently involved in the transition state, and thus that, contrary to an earlier suggestion, the reaction cannot have an SN 2 (intermediate) mechanism. No explanation ...