Thermal decomposition of t-butyl 2-nitrobenzenesulphenate

Abstract

t-Butyl 2-nitrobenzenesulphenate decomposes in refluxing anisole in the dark to give 2- and 4-methoxyphenyl 2-nitrophenylsulphides, isobutene and di-2-nitrophenyl disulphide. Aniline and p-methoxybenzenesulphonic acid were also obtained and are considered to arise from an intramolecular oxidation–reduction followed by a trans-sulphonation reaction. t-Butyl-alcohol was identified in the refluxing liquid. The initial step in the decomposition is suggested to be the heterolysis of the sulphur–oxygen bond, and the isobutene is considered to be formed by the dehydration of t-butyl-alcohol rather than by a cyclic process involving fission of the carbon–oxygen bond as previously proposed.