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Stereoselective H 2 O eliminations in 3‐ and 4‐arcylcyclohexanols under electron impact
Author(s) -
Sharvit Joseph,
Mandelbaum Asher
Publication year - 1976
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.1210110507
Subject(s) - substituent , chemistry , deuterium , stereoselectivity , labelling , ion , cis–trans isomerism , elimination reaction , stereochemistry , medicinal chemistry , organic chemistry , biochemistry , physics , catalysis , nuclear physics
The elimination of H20 from the molecular ions of trans ‐4‐ and trans ‐3‐arylcyclohexanois takes place to a greater extent than in the corresponding cis isomers. The remarkable differences in abundance taken together with substituent effects and the results of deuterium labelling, show that configuration is retained in the molecular ions which undergo the elimination, and that this process is a cis ‐1,4 and cis ‐1,3 elimination in the trans ‐4‐ and trans ‐3‐ arylcyclohexanois, respectively. Possible mechanisms for the elimination in the cis isomers are discussed.