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Stereospecific 1,3 and 1,4 dehydration reactions in the mass spectra of podocarpan‐12‐ and ‐14‐OLS †
Author(s) -
Wahlberg Inger,
Karlsson Kerstin,
Enzell Curt R.
Publication year - 1975
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.1210100303
Subject(s) - stereospecificity , dehydration , chemistry , mass spectrum , labelling , deuterium , cyclohexanol , ion , decomposition , medicinal chemistry , stereochemistry , organic chemistry , catalysis , nuclear physics , physics , biochemistry
Specific deuterium labelling revealed that podocarpan‐12α‐ and ‐14α‐01, representing conformationally well defined cyclohexanols, eliminate water mainly by stereospecific 1,3 reactions involving cis tertiary hydrogens on electron‐impact. Dehydration of podocarpan‐12ß‐0l, which also involves a cis tertiary hydrogen, occurs almost exclusively by a 1,4 reaction. Subsequent decomposition of the various [M – 18] + · ions was found to lead to different products, thus explaining some of the intensity differences encountered in the lower parts of the spectra of the epimeric podocarpan‐12‐ols and ‐14‐ols.