Bis(trimethylsilyl)methanesulfonyl and tris(trimethylsilyl)methanesulfonyl chlorides and their reactions by way of sulfenes

Abstract

Bis(trimethylsilyl)methanesulfonyl and tris(trimethylsilyl)methanesulfonyl chlorides (2c and 2d, respectively), have been prepared for the first time. Reactions of 2d with nucleophiles give products evidently derived from bis(trimethylsilyl)sulfene (1c). Reaction of 2c with piperidine gives the same piperidide as that from 2d, presumably via 1c formed by dehydrochlorination of 2c, whereas water and fluoride ion yield products consistent with their formation via trimethylsilylsulfene (1b) formed from 2c by attack at silicon with loss of the trimethylsilyl and chloro groups. No evidence for any enhanced stability in 1c was found.Key words: sulfonyl chlorides, sulfenes, silylsulfonyl chlorides, silylsulfenes, desilylation.