Novel generation of phenylnitrenium ions from S,S-dialkylanilinosulfonium salts in trifluoroacetic acid and formation of anilines by a new intramolecular hydride-shift to the phenylnitrenium ions

Abstract

Reactions of S,S-dialkylanilinosulfonium salts in trifluoroacetic acid give anilines, trifluoroacetanilides and dialkyl sulfoxides via novel intramolecular hydride-shift from the α-C–H of sulfide to phenylnitrenium ions (not completely free from the sulfide) interacting with both the unshared electron pair of the sulfide and the counter ion.