The reaction of 1, 2-dibromocyclohexane with beta-keto esters, and syntheses in the norcarane series

Abstract

Ethyl sodioacetoacetate and trans-1,2-dibromocyclohexane react in ethanol to give, in average yield, ethyl cyclohex-2-enyl-acetate, instead of the expected product, ethyl 2-(cyclohex-2-enyl)-acetoacetate, which may, however, be obtained in poor yield using a dipolar aprotic solvent. Similar results were obtained with ethyl 2-methylacetoacetate in place of ethyl acetoacetate, and a possible explanation of these findings is suggested.