Use of Tert-Butyl Sulfoxides as Latent Sulfenyl Cation Equivalents

Abstract

This paper reports a new and practical method of trifluoro-acetoxysulfenylation of olefins, starting from t-butyl sulfoxides. The latter, in a mixture of trifluoroacetic anhydride and trifluoroacetic acid, do not undergo the Pummerer reaction. Instead, sulfenyltrifluoroacetates 2 are formed and they add in situ to olefins.