✦ LIBER ✦
Skeletal rearrangement of allyl acetates after protonation by chemical ionization
✍ Scribed by J. G. Liehr; James A. McCloskey
- Publisher
- John Wiley and Sons
- Year
- 1974
- Tongue
- English
- Weight
- 344 KB
- Volume
- 9
- Category
- Article
- ISSN
- 1076-5174
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✦ Synopsis
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.