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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 10, 1980 - Issue 4
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Original Articles

An Improved Synthesis of 4-Cycloheptenone

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Pages 339-343 | Published online: 06 Dec 2006
 

Abstract

A previous paper2 described the chemistry of 1-aza-4-cyclo-octene 1 which we prepared from 4-cycloheptenone 2 according to the method of Bahurel et al.3 This procedure involves the condensation of cis-1,4-dichloro-2-butene with ethyl sodio-acetoacetate, yielding, a mixture of four isomers 3–6. The entire mixture is then heated with aqueous potassium hydroxide under reflux for four hours. Under these conditions 5 undergoes decarbethoxylation to yield 4-acetylcyclopentene 7, while 3 yields 2, presumatly by Cope rearrangement atid decarbethoxylation (2 is present in almost negligiblequantity but was reported3 to also yield 2).

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