Tetrachlorobenzyne adds to N-substituted pyrroles to give 5,6,7,8-tetrachloro-1,4-dihydronaphthalen-1,4-imines and in one case another adduct, a tetrachlorobenzo[3.4]cyclobuta[1.2-b]pyrrole; the naphthalen-1,4-imines decompose thermally by a retro-Diels–Alder reaction.
M. Ahmed and J. M. Vernon, J. Chem. Soc., Chem. Commun., 1976, 462 DOI: 10.1039/C39760000462
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