2-Phenylbenzazete (2), the first heterocyclic analogue of cyclobutadiene, is formed by vapour phase pyrolysis of 4-phenylbenzo-1,2,3-triazine; it dimerises and reacts with nucleophiles and dienes very rapidly but is surprisingly stable at –80°; 2-phenylnaphty[2,3-b]-azete (12), formed similarly, is even appreciably stable at room temperature.
B. M. Adger, M. Keating, C. W. Rees and R. C. Storr, J. Chem. Soc., Chem. Commun., 1973, 19 DOI: 10.1039/C39730000019
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