Photochemical reactions of N-(diphenylmethylene)methylthiomethylamine N-oxide. The diphenylmethylene(methylene)amine N-oxyl radical

Abstract

U.v. irradiation of the title compound in carbon tetrachloride and deuteriochloroform solutions cleanly gave benzophenone and eventually, but less cleanly, dimethyl disulphide. Initial homolysis gave the diphenylmethylene(methylene)amine N-oxyl radical which was detected and identified by e.s.r. spectroscopy. A second radical, possibly the methylthiyl radical, was observed. Subsequent reactions gave benzophenone and N-methylthiomethyleneamine, which in turn, photochemically and thermally, gave dimethyl disulphide and polymeric materials that in part involved chlorine abstraction from the solvent. The well-resolved e.s.r. spectra of the nitroxide radical have been analysed, and splitting constants have been assigned, by comparison with the spectra of partially and fully deuteriated nitroxides.