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Mass spectral hydrogen rearrangements of 1,1′‐bicycloalkyldiols under electron impact
Author(s) -
Deutsch Joseph,
Chriki Miriam
Publication year - 1979
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.1210140905
Subject(s) - deuterium , chemistry , hydrogen , hydrogen atom , electron ionization , ring (chemistry) , ion , labelling , mass spectrum , atom (system on chip) , stereochemistry , photochemistry , computational chemistry , organic chemistry , atomic physics , alkyl , ionization , physics , biochemistry , computer science , embedded system
1,1′‐Bicycloalkyl‐2,2′‐diols (mixtures of stereoisomers) and 1,1′‐diols on electron impact give rise to strong peaks equivalent to [M‐1] + ions, corresponding to cycloalkenone fragments and obviously involving hydrogen atom migrations. Deuterium labelling and substitution techniques reveal the operation of different rearrangement mechanisms for the two series of isomeric compounds. Thus, in the 1,1′‐bicycloalkyl‐2,2′‐diols a ring hydrogen atom is involved in the rearrangement, whereas in the 1,1′‐bicycloalkyl‐1,1′‐diols (pinacols) the hydroxylic hydrogen atoms migrate.