Reaction of 9-α-chlorobenzylanthracene with small nucleophiles at the ring position : differences with the behaviour of 9-anthrylbenzyl hexachloroantimonate

Abstract

The reaction of 9-anthrylbenzyl hexachloroantimonate with the nucleophiles H₂O, ^–OH, MeOH, ^–OMe, EtOH, ^–OEt, ^–OPrⁱ, and ^–N₃ gave exclusively products with the anthracene structure by attack of a nucleophile on the central carbon. By contrast, the reaction of 9-α-chlorobenzylanthracene with the same nucleophiles yielded a mixture of anthracene derivatives and compounds with a quinoidal structure. In the reaction of N-(9-benzylidene-9,10-dihydroanthracen-10-y1)-NNN-trimethylammonium chloride with ^–SPh, ^–SC₆H₄NO₂-p, and LiAlH₄, α-substituted benzylanthracenes only were obtained.