Oxidation of 3-amino-2-phenylindazole (3) or thermolysis of 3-azido-2-phenylindazole (4) gives 2-cyanoazobenzene (5) quantitatively; thermolysis or photolysis of 3-azido-2, 1-benzisothiazoles (1) induces similar ring opening to give the transient 2-cyanothionitrosobenzenes (2).
M. F. Joucla and C. W. Rees, J. Chem. Soc., Chem. Commun., 1984, 374 DOI: 10.1039/C39840000374
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