The singular reduction of 1,8-bis-hydroxymethylnaphthalene to a benzonorcaradiene by LiAlH4

[摘要] Reduction of 1,8-naphthalic anhydride (1) with LiAlH4 in THF (or DME, but not Et2O) affords, in addition to diol 2, benzonorcaradiene 3. Extended treatment of 2 or lactone 4 also leads to 3, in 66% and 65% yield, respectively. Reduction of 4 with LiAID(4) established that formation of 3 proceeds via a symmetrical intermediate. No significant norcaradiene formation is observed upon comparable LiAIH(4) treatment of 14, 15, 16 or 17. This novel reduction of a naphthalene derivative to a benzonorcaradiene appears to be unique to 2 or its precursors. (C) 1997 Elsevier Science Ltd.

[发布日期] 1997-11-24