OXIDATION OF ORGANIC AMIDE IONS BY DIOXYGEN .2. STABLE AND INTERMEDIATE PRODUCTS

The products of base-catalyzed oxidation of secondary aromatic amines were identified by the GC-MS and EPR techniques as nitroxyls, quinone nitrones, quinone imines, and for diarylamines also as the products of C-N bond cleavage-substituted nitrobenzenes, anilines and phenols. It was shown that nitroxyl radicals are the primary paramagnetic product s of the reaction and do not form by the interaction of aminyl radical s with dioxygen. A mechanism of the amide ion oxidation through the no nradical addition of dioxygen to the amide ion at the rate-limiting st age is suggested and discussed.