Persulphate oxidations. Part IX. Oxidation of biphenyl-2-sulphon-amides and o-phenoxybenzenesulphonamides

Abstract

Oxidation of biphenyl-2-sulphonamides with persulphate generated sulphonamidyl radicals which cyclised intra-molecularly to sultams. In contrast N-methyl-o-phenoxybenzenesulphonamidyl, similarly generated, rearranged to o-hydroxy-N-methyl-N-phenylbenzenesulphonamide. Oxidative cyclisation of biphenyl-2-sulphonic acid with persulphate is not practicable and gave only traces of an oxathiin.