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The triazole ring in N-chloro-4,5-diphenyltriazole (1) undergoes exceptionally mild fragmentation, most likely via the non-aromatic C-chloro isomer (2), to give the azirine (3) and hence (4); a second mode of fragmentation leading to PhCN competes.
T. C. Gallagher, M. J. Sasse and R. C. Storr, J. Chem. Soc., Chem. Commun., 1979, 419 DOI: 10.1039/C39790000419
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