Persulphate oxidations. Part 12. Generation and reactions of N-methoxy-benzamidyls and -benzsulphonamidyls
Abstract
Several N-methoxybiphenyl-2-carboxamidyls and one N-methoxybiphenyl-2-sulphonamidyl have been generated by oxidation of the corresponding N-methoxy-amides with potassium persulphate, lead tetra-acetate, or t-butoxyl radicals (from irradiated di-t-butyl peroxide), and their e.s.r. spectral parameters evaluated. The methoxyamidyls cyclise onto the adjacent aryl ring to give N-methoxyphenanthridones and/or dimerise to hydrazines which fragment spontaneously, with evolution of nitrogen, to the methyl esters of the corresponding carboxylic acids.