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Stereospecific elimination of acetic acid in 3‐ and 4‐arylcyclohexyl acetates under electron impact
Author(s) -
Sharvit Joseph,
Mandelbaum Asher
Publication year - 1978
Publication title -
organic mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0030-493X
DOI - 10.1002/oms.1210130602
Subject(s) - stereospecificity , chemistry , substituent , deuterium , acetic acid , cis–trans isomerism , medicinal chemistry , stereochemistry , organic chemistry , catalysis , physics , quantum mechanics
The elimination of CH 3 COOH 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.