Unusually facile dealkylation of alkyl 2-(methylthiomethyl)phenyl sulfoxides with triflic anhydride via dithia dications: Stereochemical and kinetic studies

Article abstract of DOI:10.1016/S0040-4039(98)02347-8

Alkyl 2-(methylthiomethyl)phenyl sulfoxides undergo facile monodealkylation on treatment with triflic anhydride in CH₃CN to afford the corresponding thiasulfonium salts and alkyl iminium salts quantitatively. The dealkylation proceeds by an S(N)1 process which gives thiasulfonium salt and alkyl cation via an initial formation of the corresponding dithia dication species.