Ball-Goodwin-Morton oxidation

What is Ball-Goodwin-Morton oxidation?

Various types of manganese dioxide MnO2 preparations have been employed as specific reagents to oxidize allyl alcohol into allyl aldehydes or ketones. The first of these manganese dioxides was reported by Ball, Goodwin, and Morton in 1948.

Ball-Goodwin-Morton oxidation uses manganese dioxide MnO2 as specific reagents to oxidize allyl alcohol into allyl aldehydes or ketones.

Ball-Goodwin-Morton oxidation - manganese dioxide MnO2
Ball-Goodwin-Morton oxidation

The Ball-Goodwin-Morton oxidation was performed initially, whereby they employed manganese dioxide MnO2 that was suspended in petroleum ether to convert vitamin A alcohol into vitamin A aldehyde.

Other oxidations of alcohols using manganese dioxide MnO2 include unsaturated steroidal alcohol, polyene alcohol, acetylenic alcohol, ferrocene alcohol, and benzyl alcohols. Interestingly, when benzyl alcohols dissolved in petroleum ether (or preferably ethyl ether) are oxidized using manganese dioxide MnO2 prepared by heating the corresponding carbonate or oxalate in air, aldehydes are produced in good yield but not for allylic alcohols. However, when acid-washed manganese dioxide suspended in petroleum ether is utilized, allylic alcohols are oxidized to the corresponding aldehydes in good yield, but not for saturated alcohols.

References

S. Ball; T. W. Goodwin; R. A. Morton “Studies on vitamin A: 5. The preparation of retinene(1)-vitamin A aldehyde.The Biochemical Journal vol. 42, 4 (1948): 516-23
DOI: 10.1042/bj0420516

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