The oxidation products of NN-dimethyl-p-phenylazoaniline

Abstract

Controlled peracetic acid oxidation of NN-dimethyl-p-phenylazoaniline gives initially NN-dimethyl-p-phenylazoaniline N-oxide, then NN-dimethyl-p-(phenyl-ONN-azoxy)aniline N-oxide and NN-dimethyl-p-(phenyl-NNO-azoxy)aniline N-oxide, and finally p-nitrophenyl-ONN-azoxybenzene, p-nitrophenyl-NNO-azoxybenzene and 4,4′-di(phenyl-NNO-azoxy)azoxybenzene. NN-Dimethyl-p-(phenyl-ONN-azoxy)aniline and NN-dimethyl-p-(phenyl-NNO-azoxy)aniline could be prepared from the corresponding N-oxides by means of sodium arsenite. Some azoxy isomerisations have been observed to occur by the action of heat, or concentrated sulphuric acid. The latter also causes the conversion of NN-dimethyl-p-phenylazoaniline N-oxide, or NN-dimethyl-p-(phenyl-ONN-azoxy)aniline N-oxide into NN-dimethyl-p-(4-hydroxyphenylazo)aniline and other products. The former reaction involves the rearrangement of an oxygen function to a p-phenyl position ten atoms distant.