Synthesis and radical decomposition of α-hydroxydiazenes. II. tert-Butylazodiphenylcarbinol

Abstract

tert-Butylazodiphenylcarbinol (Ph2C(OH)N=NCMe3, 3) decomposes in oxygen-free benzene by the unimolecular radical mechanism characteristic of most azo compounds. In benzene or in carbon tetrachloride, with or without air present, decomposition of 3 is also induced by radicals through abstraction of hydroxyl hydrogen in concert with the formation of nitrogen. Radicals which induce decomposition of 3 include trichloromethyl, tert-butyl, phenylthiyl, tert-butylperoxy and possibly oxygen. The failure of inhibitors like thiophenol to stop chain decomposition of 3 is interpreted in terms of the thermochemistry of induced decomposition.