Dehydrochlorination of some naphthalene tetrachlorides and related compounds. Part III. Structure and dehydrochlorination of a 1,2,3,4-tetrachloro-1-phenyltetralin

Abstract

Chlorine reacts with 1-phenylnaphthalene in chloroform to give, among other products, a tetrachloride which has been characterised from its ¹H n.m.r. spectrum as r-1,c-2,t-3,t-4-tetrachloro-1-phenyltetralin. On alkaline dehydrochlorination, it gives 2,3-dichloro-1-phenylnaphthalene almost exclusively; when heated in carbon disulphide or when treated in nitromethane with an excess of aluminium trichloride, it gives 2,4-dichloro-1-phenylnaphthalene and 2,3-dichloro-1-phenylnaphthalene in a ratio of ca. 2 : 1 or greater. The mechanistic implications of these results are discussed.