Thermal decomposition of 2-dimethylamino-3-methylbenzazide produced, instead of the expected isocyanate, a high yield of the isomeric cyclised product 1,1,7-trimethylindazol-3-ylio oxide; a single-crystal X-ray diffraction study shows delocalisation of the negative charge though little conjugation of the unsaturation of the five-membered ring with the benzene ring.
N. M. Waldron, M. Montevalli, S. Azam and P. C. Dasopoulos, J. Chem. Soc., Chem. Commun., 1995, 81 DOI: 10.1039/C39950000081
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