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Hydrogen rearrangements in alkyl‐, styryl‐ and alkyl propenyl sulfoxides
Author(s) -
Liu Lilian Kao,
Su C. Y.,
Li WenShan
Publication year - 1989
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.1210240508
Subject(s) - propenyl , alkyl , chemistry , cyclopropane , alkene , hydrogen , regioselectivity , deuterium , medicinal chemistry , stereochemistry , organic chemistry , ring (chemistry) , catalysis , physics , quantum mechanics
The McLafferty‐type rearrangements, which are the most facile fragmentation for the styryl‐ and the alkyl propenyl sulfoxides, have been proven to involve at least a β‐hydrogen by deuterium labelling studies. γ‐Hydrogen also rearranges, yet a cyclopropane instead of an alkene is eliminated. Furthermore, alkyl propenyl sulfoxides undergo hydrogen migration only to the surfinyl oxygen.