Oxidation, thermolysis, and photolysis of diarylsulphamides

Abstract

In contrast with NN′-dialkylsulphamides the oxidation of diarylsulphamides by hypochlorite is not a general route to aromatic azo-compounds; instead the major products are usually quinone anils, formed in a new aromatic rearrangement. The photolysis of the arylsulphamides and the thermolysis of their NN′-dichloro-derivatives do give azo compounds, however. The photochemical reaction appears to be intramolecular, possibly involving extrusion of sulphur dioxide as the first step.