Thermal reactivity of 4′-substituted- and 4′-substituted-2-phenyl-benzenesulphenanilides

Abstract

The thermal decomposition of 4′-nitro-, 4′-H-, and 4′-methoxy-benzenesulphenanilides in benzene and/or furan, and of 4′-substituted-2-phenylbenzenesulphenanilides (1d–f) in benzene, was found to proceed by two distinct pathways: (i) nucleophilic displacement by furan and/or another sulphenanilide unit and (ii) homolytic S–N bond fission to give sulphenyl and anilino radicals. An increase in the electron-withdrawing capability of the 4′-substituent favours the ionic pathway, whereas the radical pathway is favoured by an increase in the reaction temperature.