Oxidative, photoinduced, and thermal sulphur–nitrogen bond fission in benzenesulphenanilides

Abstract

The reaction of NN-bis-p-methoxyphenylbenzenesulphenamide (1) in liquid sulphur dioxide afforded bis-p-methoxyphenylamine, diphenyl disulphide, p-methoxyanilino-5-methoxyphenyl phenyl sulphide, and 5,10-di-hydro-2,7-dimethoxy-5,10-bis-p-methoxyphenylphenazine through oxidative cleavage of the S–N bond of (1). The reaction of the sulphenamide (1) with aniline in liquid sulphur dioxide gave benzenesulphenanilide, suggesting the formation of benzenesulphenylium ion in this solvent. Rearrangement products were also obtained by thermolysis and photolysis of some sulphenanilides.