ISSN:
0030-493X
Keywords:
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The presence of a 15-hydroxy substituent in naturally-occurring kaurenes and gibberellins gives rise to a structurally diagnostic ion at m/z84 (C5H8O) in their electron-impact mass spectra, which shifts to m/z156 for the TMS derivative, and is unaffected by differences in the A and B rings. Studies on a model tricyclic system have shown that this ion is more intense when the stereochemistry of the B/C ring junction is cis than when it is trans. In accordance with a previously proposed pathway for the formation of this ion, deuterium labelling confirms that there is a site-specific transfer of the β-hydrogen from the cis ring junction to the C5 fragment ion, although a minor modification of the earlier mechanism is proposed.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/oms.1210240811
Permalink