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Side-Chain Oxidation of Some Phenyl-Substituted Alcohols in Aqueous Solution: Formation and Fragmentation of Radical-Cations

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The reactions of the hydroxyl radical (at low pH) and SO-4 have been employed to oxidize a number of phenyl-substituted alcohols in aqueous solution; ESR spectroscopy has been employed to study directly the radicals formed by fragmentation of first-formed radical-cations. Examples of deprotonation (to give benzyl radicals), Cα-Cβ bond scission (e.g. PhCH2 CH2 OH to PhCH2.) and longer-range fragmentation (e.g. PhCH2 CH2 CMe2 OH to PhCH2 CH2.) are described and discussed: evidence is obtained for intramolecular nucleophilic attack as a route for overall electron-transfer from side-chain to aromatic ring. Solvation of the proton and of oxygen-conjugated carbonium ions is thought, at least in part, to account for differences between fragmentations induced in the gaseous and aqueous phases.

Affiliations: 1: Department of Chemistry University of York Heslingston, York YO1 5DD England


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