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Electron impact induced water elimination from hydroxyamides. 2— N ‐acetyl‐ and N ‐benzoyl‐4 a ‐hydroxydecahydroquinoline and N ‐Methyl‐4 a ‐hydroxy‐2‐oxodecahydroquinoline
Author(s) -
Steiner B.,
Schumann D.,
Naumann A.
Publication year - 1983
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.1210180809
Subject(s) - chemistry , hydrogen , diastereomer , medicinal chemistry , ion , metastability , stereochemistry , organic chemistry
Abstract Electron impact induced water elimination from the metastable molecular ions of N ‐acetyl‐ and N ‐benzoyl‐4 a ‐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 H 2 O loss from both diastereomers of N ‐methyl‐4 a ‐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.