Issue 10, 1997

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.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1997, 2095-2098

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

G. W. Wijsman, L. A. van der Veen, W. H. de Wolf and F. Bickelhaupt, J. Chem. Soc., Perkin Trans. 2, 1997, 2095 DOI: 10.1039/A700605E

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