Nucleophilic substitution at silicon: evidence for a parallel with addition reactions to α,β ethylenic ketones
Abstract
The relationship between the stereochemistry of nucleophilic substitution at Si–O and Si–F bonds and the electronic character of the attacking nucleophile (Bu2iAlH, LiAlH4, LiAlH4–4CuI, EtLi, EtMgBr, and Et2CuMgBr) has been studied; those reagents which favour 1,2-addition to α-enones react with retention of configuration, whereas those which favour 1,4-addition to α-enones react with inversion.