The free radical chemistry of the azoxy group

Abstract

The azoxy functional group, though relatively uncommon, is found in several natural products and in liquid crystalline compounds. Azoxyalkanes are generally very stable to heat and light and are not subject to attack by radicals. Intramolecular radical reactions, however, can lead to cyclic aminyl nitroxides and hydrazyls, which rearrange further or undergo fragmentation. The azoxy group greatly stabilizes an attached carbon-centered radical but the chemistry of the resulting alpha-azoxy radicals is not completely understood.