
%0 Journal Article
%A Dyall, LK 
%A Kemp, JE 
%T Oxidative cyclizations. I. The mechanism of the oxidation of ortho-substituted anilines with phenyliodoso acetate
%J Australian Journal of Chemistry
%D 1967/08/01
%V 20
%N 8
%P 1625-1633
%K 
%R https://doi.org/10.1071/CH9671625
%U https://www.publish.csiro.au/paper/CH9671625 
%X A comparison has been made of the types of ortho substituents which can be incorporated into a new heterocyclic ring by pyrolysis of aryl azides or during oxidation of anilines with phenyliodoso acetate. The results enable a new mechanism to be proposed for the amine oxidation. In its key step, the ortho substituent displaces iodobenzene from an intermediate iodoso ester to form the cyclic oxidation product. A competing reaction path involves homolysis of this iodoso ester to yield the free-radical precursors of azo compounds. 
