Oxidation of organic amide ions by dioxygen 2. Stable and intermediate products

Article abstract of DOI:10.1007/BF00703479

The products of base-catalysed oxidation of secondary 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 products of the reaction and do not form by the interaction of aminyl radicals with dioxygen.A mechanism of the amide ion oxidation through the nonradical addition of dioxygen to the amide ion at the rate-limiting stage is suggested and discussed. - Key words: aromatic amines, amide ions, oxidation, dioxygen, mechanism, nitroxyl radicals, synthesis.