Oxidation with metal oxides-VIII: oxidation of bisphenylhydrazones of 1,2-diketones with nickel peroxide

Balachandran, K. S. ; Hiryakkanavar, I. ; George, M. V. (1975) Oxidation with metal oxides-VIII: oxidation of bisphenylhydrazones of 1,2-diketones with nickel peroxide Tetrahedron, 31 (9). pp. 1171-1177. ISSN 0040-4020

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/004040...

Related URL: http://dx.doi.org/10.1016/0040-4020(75)85053-8

Abstract

The nickel peroxide oxidation of bisphenylhydrazones of 1,2-diketones gives rise to a variety of products such as bisphenylazoolefins, phenylazopyrazoles and triazoles, depending on the reaction conditions. Thus, glyoxal bisphenylhydrazone in benzene at room temperature gave bisphenylazoethylene5a, whereas methylglyoxal bisphenylhydrazone gave a mixture of bisphenylazoolefin10a and phenylazopyrazole14a. The oxidation of phenylglyoxal bisphenylhydrazone, on the other hand, gave a mixture of the triazole33 and a tetraazapentalene derivative40. Reasonable mechanisms for the formation of the various oxidation products have been suggested.

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