Polyhalogenoheterocyclic compounds. Part XXIX. Perchloro-acridine, -phenanthridine, and -benzo[h]quinoline

Abstract

Perchloro-acridine, -phenanthridine, and -benzo[h]quinoline have been synthesised by direct chlorination of the corresponding heterocyclic compound or its monochloro-derivative, complexed with aluminium trichloride. Attempts to replace chlorine by fluorine, by using potassium fluoride under a variety of conditions, were unsuccessful. Hydrolysis of the acridine and phenanthridine derivatives gave the corresponding 9-acridone and phenthridin-6-one, respectively. The orientation of nucleophilic substitution is established and there is no evidence for competing reductive dechlorination in reactions with amines.