Tetrahedron

Nucleophilic substitutions at silicon: Evidence for ion-pair dissociation as controlling factor of the stereochemistry and a simple mechanistic proposal

RJP Corriu, C Guerin

Index: Corriu, R. J. P.; Guerin, C. Tetrahedron, 1981 , vol. 37, # 14 p. 2467 - 2472

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Citation Number: 11

Abstract

Stereochemical and kinetic data are reported for reactions between organolithiums or LiAlH4 and some chiral organosilanes. They rule out a mechanism involving complexation control, such as the SNi-Si process proposed by Sommer et al. Electrophilic assistance to the cleavage of a Si-X bond does not control the stereochemistry, but acts as an additional factor which can facilitate the inversion by increasing the ability of the leaving group to ...