New one-pot synthesis of a benzonorcaradiene derivative by reduction of naphthalic anhydride with LiAlH4

Abstract

Reaction of naphthalic anhydride (naphthalene-1,8-dicarboxylic anhydride) (1) or of 1,8-bis(hydroxymethyl)naphthalene (3) with LiAlH₄ in refluxing 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 by the assistance of a neighbouring alkoxide function.