The chlorosulfonyl moiety as a leaving group: hydride reduction of sulfonyl chlorides

Abstract

A series of γ-sulfone sulfonyl chlorides undergo a novel reduction upon reaction with lithium aluminum hydride to furnish the corresponding ethyl sulfones. The reactions appear to proceed in an S N 2 fashion with the chlorosulfonyl moiety functioning as the leaving group. In general sulfonyl chlorides furnish mercaptans as hydride reduction products.A novel two-phase hydrolysis is shown to convert a thiol ester to a symmetric sulfide which involves hydrolysis and an S N 2 displacement in the aqueous phase.