Abstract

Elimination of CH3OH under electron impact occurs in trans-1,2- and 1,3-dicarbomethoxycycloalkanes to a greater extent than in the cis-isomers. In the trans-diesters, one of the α-hydrogen atoms is abstracted in the course of the elimination. In the methyl esters of cyclohexane 1,4-dicarboxylic acids, the elimination of CH3OH is also specific to the trans-isomer, but the abstracted hydrogen atom does not originate at the α-position. This result is explained by a stereospecific hidden hydrogen migration step, preceding the elimination.

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