Superoxide ion acts as a mild and highly selective oxidizing agent for aromatic amines. Aniline and a-naphthylamine were not oxidized, but ß-naphthylamine formed dibenzo[a,h]phenazine, dibenzo- [a,i]phenazine and 2,2'-azonaphthalen-1-ol. o -and p -Diamines are oxidized to diaminoazobenzenes but m -diamines are unreactive. Similarly o - and p -aminophenols are oxidized to dihydroxyazo- benzenes but m -aminophenols are unaffected, and o -mercaptoaniline forms the disulfide. The oxidations are considered to be free-radical processes, initiated by hydrogen abstraction by superoxide from the substrates. The biological significance of the results is discussed.
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Crank et al. (1984) studied this question.