Photooxygenation of Acetone Hydrazone: Characterization of an Unstable Intermediate

Article abstract of DOI:10.1021/jo00217a034

The tetraphenylporphyrin-sensitized photooxygenation of acetone hydrazone produces 2-4percent of an unstable compound with a 1H NMR spectrum consisting of singlets at 1.3 (6 H), 13.7 (1 H), and 15.8 (1 H) ppm.The structure assigned is that of the hydroperoxy diazene (azo hydroperoxide) (CH3)2C(OOH)N=NH.The compound decomposes very rapidly above -20 deg C with a high yield of formation of N2 but no O2 (: > 100:1).Photooxygenation of either acetone hydrazone or benzophenone hydrazone in toluene gives 10-20percent yields of cresols.