Abstract
The relationship between the stereochemistry of nucleophilic substitution at silicon and the electronic character of the attacking nucleophile has been studied. It is shown that the reagents which flavour 1,2-addition to α-enones react with retention of configuration, whereas those which favour 1,4-addition react with inversion at silicon. This is consistent with our hypothesis suggesting that the dominant influence on the stereochemistry at silicon for a given leaving group is the electronic character of the nucleophile: inversion would be a frontier-orbital process, and retention a charge-controlled mechanism.
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