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The mechanism of the loss of H 2 and H 2 O from 1,4‐cyclohexanediol anion and related compounds
Author(s) -
Gäumann T.,
Stahl D.,
Tabet J. C.
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.1210180608
Subject(s) - chemistry , ion , deuterium , stereospecificity , dissociation (chemistry) , ionization , alkoxide , hydrogen , photochemistry , inorganic chemistry , organic chemistry , catalysis , atomic physics , physics
Losses of H 2 and H 2 O from the [M‐H] − alkoxide anions of 1,4‐cyclohexanediol formed in OH − negative chemical ionization were studied using synthetic deuterated analogues and labelling by hydrogen‐deuterium exchange between neutrals in the ion source prior to ionization. Simple 1,2‐H 2 elimination leading to an enolate ion does not occur, but stereospecific mechanisms are shown to give a ketolate intermediate daughter ion. Collisionally activated dissociation spectra of the resulting daughter ions are the same as those of the corresponding ions generated directly from ketols.