Article ID Journal Published Year Pages File Type
5218808 Tetrahedron 2012 11 Pages PDF
Abstract

Oxone (peroxysulphate) very efficiently oxidizes benzene to p-quinone (TON 1140) and alkanes to the corresponding alcohols and ketones (aldehydes) in aqueous acetonitrile 50 °C if catalytic amounts of complex [Mn2L2O3]2+ (L=1,4,7-trimethyl-1,4,7-triazacyclononane) and oxalic acid are present in the solution. In contrast to the similar reaction with H2O2, the alkane oxidation with Oxone does not afford the corresponding alkyl hydroperoxides. Phenol was quantitatively oxidized to a mixture of p-quinone and pyrocatechol (9:1 ratio). Cyclohexanol gave cyclohexanone (TON 400). The proposed mechanism includes the formation of an oxidizing species containing the Mn(V)O fragment. A kinetic study demonstrated that an adduct of [Mn2L2O3]2+ and oxalic acid is formed in the initial stage. This adduct reacts with Oxone to generate the oxidizing species.

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Physical Sciences and Engineering Chemistry Organic Chemistry
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