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

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.