Electron spin resonance studies. Part 71. Side-chain oxidation pathways in the reactions of ˙OH and SO4–˙ with some phenyl-substituted carboxylic acids, their anions, and some related compounds
- 1 January 1987
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 3,p. 371-380
- https://doi.org/10.1039/p29870000371
Abstract
A series of arene radical-cations has been generated in situ by the reactions of methylbenzene, phenylethanoic acid, 3-phenylpropanoic acid, and some derivatives and cyclic analogues with both SO4 –˙ and ˙OH (the latter in acid solution). The results are interpreted in terms of a variety of subsequent rapid reactions including hydration, deprotonation (to give benzylic radicals), and fragmentation (decarboxylation): for a series of radical-zwitterions +˙Ar(CH2)nCO2 –(n= 1–3) decarboxylation (k 109 dm3 mol–1 s–1) appears to proceed via direct intramolecular electron-transfer, though in some cases formation of a discrete σ-bonded intermediate cannot be ruled out.Keywords
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