Oxidation of the hydrazones of o-aminophenyl alkyl and aryl ketones provides a simple route to the previously virtually unknown 4-alkyl- and 4-aryl-1,2,3-benzotriazines; 1-(o-azidophenyl)diazoethane on thermolysis also gives the 4-methyltriazine in high yield; on pyrolysis in the vapour phase, the triazines fragment to give benzyne and hence biphenylene (40%).
S. Bradbury, M. Keating, C. W. Rees and R. C. Storr, J. Chem. Soc. D, 1971, 827 DOI: 10.1039/C29710000827
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