Dibenzothiepin Derivatives and Related Compounds. II. A Novel Cyclization Reaction of 6-Chloro-11-phenyl-6, 11-dihydrodibenzo [b, e] thiepins

Abstract

By the reaction of 11-chloro-11-phenyl-(II) and 11-phenyl-6, 11-dihydrodibenzo-[b, e] thiepin (III) with NCS 6, 11-dichloro-(I) and 6-chloro-11-phenyl-6, 11-dihydrodibenzo-[b, e] thiepin (XV) were prepared, respectively. The compound (I) reacted with water or aqueous ammonia to afford a new heterocyclic compound, 6, 11-epoxy-(V) or 6, 11-epimino-11-phenyl-6, 11-dihydrodibenzo [b, e] thiepin (VIII), respectively. On heating in proper solvent, I or XV underwent a novel cyclization to form a bridged compound (IX, XIII or XIV). The radical mechanism for the new cyclization was proposed.