Anchimeric assistance of the sulfinyl group in the hydrolysis of cyano groups: A new mild method for the reduction of sulfoxides.

Conditions to achieve reductive hydrolysis of beta-cyanosulfoxides into their corresponding beta-sulfenylamides are reported. The anchimeric assistance of the sulfinyl oxygen in the hydrolysis of the cyano group is proposed to explain the mild conditions required to achieve it and several proofs supporting this assumption are indicated. From these results a new mild method to transform sulfoxides into sulfides has been developed. Copyright (C) 1996 Elsevier Science Ltd