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Skeletal rearrangement of allyl acetates after protonation by chemical ionization
Author(s) -
Liehr J. G.,
McCloskey James A.
Publication year - 1974
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.1210090506
Subject(s) - chemistry , intramolecular force , substituent , protonation , ring (chemistry) , deuterium , hydrogen atom abstraction , medicinal chemistry , photochemistry , carbon monoxide , mass spectrum , stereochemistry , hydrogen , mass spectrometry , organic chemistry , catalysis , ion , physics , quantum mechanics , chromatography
Abstract In the methane chemical ionization mass spectra of allyl phenylacetate and allyl phenoxyacetate the major reaction paths (>40%σ) involve skeletal rearrangements, which have no analogy in the corresponding, simpler electron‐impact spectra. Substituent and deuterium labeling studies suggest a mechanism involving intramolecular substitution of the phenyl ring by the allyl group. Abstraction of hydrogen from the ortho position of the phenyl ring or from the rearranged allyl group is followed by expulsion of water and carbon monoxide.