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Electron impact induced hydrogen rearrangements in ( Z )‐ and ( E )‐styryl alkyl sulfoxides
Author(s) -
Liu Lilian Kao,
Luo FenTair
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.1210180106
Subject(s) - alkyl , alkene , chemistry , yield (engineering) , alkane , medicinal chemistry , hydrogen , beta hydride elimination , carbon fibers , oxygen , photochemistry , organic chemistry , hydrocarbon , catalysis , materials science , metallurgy , composite number , composite material
Alkene elimination, alkyl loss, styryl and alkyl migrations to oxygen are the major fragmentations of (Z)‐ and ( E )‐alkane‐sulfinyl‐2‐phenylethenes ( cis ‐ and trans ‐styryl alkyl sulfoxides) under electron impact. Alkene elimination has been found to go through a McLafferty‐type hydrogen rearrangement to yield the benzylic carbon and the sulfinyl oxygen, respectively. This is the most facile and interesting process for compounds with longer alkyl chains (R⩾C 3 H 7 ), and is a unique feature for styryl sulfoxides. Product ion analyses show the migrating aptitude to carbon and to oxygen to be qualitatively similar.