Naphthalene tetrachlorides and related compounds. Part 12. Influence of some 1-substituents on the course of chlorination of derivatives of 2-naphthol

Abstract

The chlorinations of 1-methyl-2-naphthol, 1-bromo-2-naphthol,2,2′-dihydroxy-1,1′-dinaphthylemethane, and 6-t-butyl-2-naphthol with excess of chlorine in acetic acid give tetralin-2-ones analogous to that formed from 1-chloro-2-naphthol. 1,6-Di-t-butyl-2-naphthol, however, gives only 1,6-di-t-butyl-1,3-dichloro-1,2-dihydronaphthalene; 1-iodo-2-naphthol gives some 1,1,3,4-tetrachlorotetralin-2-one in acetic acid, whereas in chloroform it gives a mixture from which r,-1,c-2,t-3,t-4,5,7-hexachlorotetralin-6-ol was isolated. The structures of these products and the pathways leading to them are discussed.