Abstract
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.
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