Reaction of 9-α-chloronaphthylmethylanthracene and its homologues with nucleophiles under solvolytic conditions. Effect of the increase of bulk at C-α on the reaction site

Abstract

The reaction of 9-α-chloronaphthylmethylanthracene and its homologues with (a) sodium ethoxide in ethanol, (b) ethanol in the presence of triethylamine, (c) sodium borohydride in aqueous diglyme, and (d) sodium azide in aqueous NN-dimethylformamide has given a mixture of substituted anthracenes and 9,10-dihydroanthracenes. The yield of the latter increases as the aryl group at C-α becomes larger. The phenyl ring of a chloride at C-10 causes the reaction at this position to be retarded. The relative thermodynamic stabilities between the anthracenes and the 9,10-dihydroanthracenes have been investigated.