Issue 0, 1968

Electron spin resonance studies. Part XIV. Hydroxylation. Part III. Reactions of anisole, acetanilide, fluorobenzene, and some phenols with the titanium(III)–hydrogen peroxide system

Abstract

When oxidised by the Ti(III)–hydrogen peroxide system in particular ranges of acidity, phenol, quinol, m- and p-fluorophenol, p-chlorophenol, and fluorobenzene each form one or more radical adducts, by combination with the hydroxy-radical, which are observable by electron spin resonance spectroscopy. These adducts are susceptible to acid- and/or base-catalysed reactions to give other radicals whose spectra can be observed; e.g., in a strongly acid medium, those from both phenol and fluorobenzene give, by different mechanisms, the phenoxy-radical. The spectra of adducts of anisole and of acetanilide with the hydroxy-radical have not been detected spectroscopically, although other observations provide evidence for their formation; these species are apparently more rapidly destroyed than the parent member of the series (the hydroxycyclohexadienyl radical), and possible destruction processes, for both weakly and strongly acidic media, are discussed.

Article information

Article type
Paper

J. Chem. Soc. B, 1968, 48-53

Electron spin resonance studies. Part XIV. Hydroxylation. Part III. Reactions of anisole, acetanilide, fluorobenzene, and some phenols with the titanium(III)–hydrogen peroxide system

C. R. E. Jefcoate and R. O. C. Norman, J. Chem. Soc. B, 1968, 48 DOI: 10.1039/J29680000048

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