Novel reactivity of (9-anthryl)diphenylmethyl hexachioroantimonate and related compounds with nucleophiles at the ring position

Abstract

The reactions of (9-anthryl)diphenylmethyl hexachloroantimonate (1) with nucleophiles gave mainly the quinoidal products by attack on the 10-position of the anthracene ring, suggesting the existence of a strong interaction of the two phenyl rings with the hydrogens at the 1- and 8-positions of the anthracene ring. Compound (1) is propellorshaped, and thus approach by the nucleophile to the benzylic site is difficult. For the reactions of 9-diphenylmethylene-10-chloro-9,10-dihydroanthracene, data were obtained which suggest that the approach of the nucleophile to the 10-position of anthracene ring is more hindered than the case of (1). By substituting the 10-hydrogen of (1) with a phenyl group, a remarkable retardation of attack by nucleophiles on position 10 was observed.