Solid nickel peroxide has been shown to be capable of oxidizing aromatic primary amines to the corresponding azo-compounds in benzene solution. Benzylamine and its derivatives bearing a substituent in the benzene ring could be easily oxidized by the same oxidant to give the corresponding nitriles in good yields regardless of the position and the variety of a substituent. Alkyl amines also underwent similar oxidation. In addition, the mechanisms of these oxidations were discussed.
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Nakagawa et al. (1963) studied this question.