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Oxidation of Benzyl Alcohols with Manganese Dioxide


SINCE the time that Ball, Goodwin and Morton1 first used manganese dioxide to oxidize vitamin A to retinene, many investigators have used this reaction. Evans2 has summarized much of the uses and Gritter and Wallace3 have carried out an extensive investigation with regard to the efficiency of numerous manganese dioxides on the yields of the oxidations. Mechanistic considerations were present from the very beginning since Ball, Goodwin and Morton1 suggested that the oxidation occurred on the surface of the dioxide, Henbest4 suggested that the reaction was occurring by free radical intermediates on the surface of the dioxide and Pratt and van de Castle5 found that these intermediates would explain their results obtained with substituted benzyl alcohols. The latter authors proposed a mechanism consistent with the results available and it was one which could apply to compounds other than unsaturated alcohols6. The present study was concerned with rate changes with solvent, temperature, type of manganese dioxide and the conclusion which the evidence would permit about what is occurring on the surface of the dioxide in the oxidation.

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GRITTER, R., DUPRE, G. & WALLACE, T. Oxidation of Benzyl Alcohols with Manganese Dioxide. Nature 202, 179–181 (1964).

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