The structure of the product ion of a ‘McLafferty’ rearrangement
✍ Scribed by J. G. Beynon; R. M. Caprioli; T. W. Shannon
- Publisher
- John Wiley and Sons
- Year
- 1971
- Tongue
- English
- Weight
- 384 KB
- Volume
- 5
- Category
- Article
- ISSN
- 1076-5174
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✦ Synopsis
A series of alkylphenylketones has been examined. Whenever the alkyl chain is three or more carbon atoms long, the well-known McLafferty rearrangement occurs with elimination of the elements of a neutral olefin. The further fragmentation of the ion formed in this rearrangement reaction has been studied using the technique of ion kinetic energy (IKE) spectroscopy. The measured release of kinetic energy has been used to show that the rearrangement ion has an enolic type structure.
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It is shown by deuterium labelling, linked-scan measurements and collision activation that the [M -C,H,'I+ (a-cleavage) ion in the electron impact ionization spectrum of tributylamine loses C3H, with transfer of one hydrogen specifically from the y-position. The experimental data point towards a mec