Tetrahedron Letters

Synthesis of azulene from 6-acyloxyfulvenes

YN Gupta, SR Mani, KN Houk

Index: Gupta, Y. N.; Mani, S. R.; Houk, K. N. Tetrahedron Letters, 1982 , vol. 23, # 5 p. 495 - 498

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Citation Number: 7

Abstract

Abstract The 6-acetoxy, tosyloxy, and p-nitrobenzoyloxy derivatives of fulvene undergo [6+ 4] cycloadditions with 1-diethylaminobutadiene to give azulene in 12, 14, and 68% yield, respectively. The p-nitrobenzoyloxyfulvene is a crystalline, stable substance which is highly reactive towards nucleophilic dienes.

~12%

~14%

~70%

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