ISSN:
0030-493X
Keywords:
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Electron impact induced water elimination from the metastable molecular ions of N-acetyl- and N-benzoyl-4a-hydroxydecahydroquinoline mainly follows a formal [1,2] elimination. The initiating and ratedetermining step in the reaction is the hydrogen rearrangement from C-8a onto the carbonyl group. The transferred hydrogen is subsequently lost, together with the hydroxyl group. The almost complete absence of H2O loss from both diastereomers of N-methyl-4a-hydroxy-2-oxodecahydroquinoline confirms that the reaction can only proceed when the carbonyl group is able to function as ‘hydrogen carrier’ by occupying positions in the vicinity of both a hydrogen and the hydroxyl function.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/oms.1210180809
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