Stereospecific elimination of acetic acid in 3- and 4-arylcyclohexyl acetates under electron impact

The elimination of CH₃COOH from the molecular ions of trans-3- and 4-arylcyclohexyl acetates takes place to a greater extent than in the cis isomers. Deuterium labelling shows that the elimination involves mainly the benzylic hydrogen in the trans-acetates, but not in the cis isomers. This behaviour is similar qualitatively to that of the corresponding alcohols and methyl ethers, but entirely different from that of t-butylcyclohexyl acetates, which do not exhibit any stereospecificity. Substituent effects on the elimination for both cis and trans isomers are discussed.