1-Phenylazo-l-hydroperoxycyclohexanes, easily prepared by the autoxidation of cyclohexanone phenyl hydrazones, have been found to undergo C (1)–C (2) bond cleavages when treated with acids, bases, or reducing reagents under mild conditions. Thus 6-oxoalkanoic acids and their derivatives have been obtained in good yields from 2- hydroxycyclohexanone derivatives. The 2-hydroxyl group seems to play an important role ...