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Stereospecific 1,3 and 1,4 dehydration reactions in the mass spectra of podocarpan-12- and -14-OLS†

✍ Scribed by Inger Wahlberg; Kerstin Karlsson; Curt R. Enzell

Publisher
John Wiley and Sons
Year
1975
Tongue
English
Weight
890 KB
Volume
10
Category
Article
ISSN
1076-5174

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✦ Synopsis

Abstract

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.

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