The mechanism of solvolysis of 2-halogenoalkylsilanes. Part I. Steric aspects

Abstract

The solvolysis of erythro-1,2-dibromopropyltrimethylsilane in aqueous ethanol at room temperature has been shown to result in the highly stereospecific trans-elimination of trimethylbromosilane. A mechanism is suggested which involves initial cleavage of the carbon–halogen bond assisted by participation of the silicon with the developing positive charge on the carbon atom.