Reduction-Elimination of Vicinal Cyanohydrins

Abstract

The reduction of aliphatic nitriles to alkanes by dissolving metals has been known for some time.¹ Presumably, this interesting cleavage reaction proceeds via election transfer first through an alkyl radical and then an organometallic (carbanion-type) species which undergoes protonation by solvent (Scheme I). In recent years we have sought to employ the presumed carbanionic species as an intermediate which could initiate chemistry of synthetic interest.²findings which show that the foregoing concepts can be applied to the synthesis of olefins from vicinal cyanohydrins.