
%0 Journal Article
%A Crank, G 
%A Makin, MIH 
%T Oxidations of aromatic amines by superoxide ion
%J Australian Journal of Chemistry
%D 1984/04/01
%V 37
%N 4
%P 845-855
%K 
%R https://doi.org/10.1071/CH9840845
%U https://www.publish.csiro.au/paper/CH9840845 
%X Superoxide ion acts as a mild and highly selective oxidizing agent for aromatic amines. Aniline and &#945;-naphthylamine were not oxidized, but &#946;-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. 
