Abstract

The oxidations of three benzyl ethers and diphenyl ether in aqueous methyl cyanide solution are essentially first-order with respect to both substrate and oxidant. The overall reactivities are in the sequence PhCH2OMe < PhCH2OCH2Ph < PhCH2OC6H11 < PhOPh. The oxidations are faster than those of similar hydrocarbons, but very much slower than that of benzyl alcohol. An outer sphere mechanism of oxidation is suggested. Quantitative analyses show that the oxidation products from the benzyl ethers are benzaldehyde, benzoic acid, and sometimes the corresponding benzoate ester. Attack occurs on the benzylic CH2 group, and there is negligible ring fission.

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