The Hetarynes

Investigations carried out during the last six years have shown that, as in the case of benzene, an extra bond can be introduced into heteroaromatic rings. Since this possibility does not appear to be confined to exceptional cases, the heterocyclic arynes (hetarynes) promise a much wider variety than the carbocyclic arynes. Hetarynes occur mainly as intermediates in nucleophilic substitutions on halogenated heterocyclic compounds. Since the replacement of a CH group in dehydrobenzene by a nitrogen atom and the condensation of benzene rings have stabilizing effects, the stability of hetarynes is expected to increase with the number of N atoms and with the number of condensed aromatic rings.