NEW ONE-POT SYNTHESIS OF A BENZONORCARADIENE DERIVATIVE BY REDUCTION OF NAPHTHALIC ANHYDRIDE WITH LIALH4

Reaction of naphthalic anhydride (naphthalene-1,8-dicarboxylic anhydri de) (I) or of 1,8-bis(hydroxymethyl)naphthalene (3) with LiAlH4 in ref luxing THF yields the benzonorcaradiene derivatives 2 in yields of up to 50%. It is proposed that in the formation of this (strained)product an anti-hydroalumination reaction is involved, which Is facilitated b y the assistance of a neighbouring alkoxide function.