Stereochemical control of the reaction of chlorosilane with methyllithium by the addition of metal cyanide: Inversion by potassium cyanide and retention by copper(I) cyanide

Abstract

In the 1,4-dichlorotetrasilane derivative composed of disilane units bearing two pentamethylene tethers, the substitution of a chlorine atom on the silicon atom by the methyl group during the reaction with methyllithium mainly proceeds with inversion of configuration of the silicon atoms, (1) the yield being dramatically improved by the addition of potassium cyanide, and (2) the stereochemistry being changed to retention of configuration by the addition of copper(I) cyanide.