Oxidative cleavage of ketones

Oxidative Cleavage of Ketones. Aldehydes, and Alcohols Cycloalkanone oxidative ring opening... 

Fig. 102 Mn(II)-Co(II)-catalyzed oxidative cleavage of ketones to benzoic acids...

The Baeyer-Villiger rearrangement often is called Baeyer-Villiger oxidation (see the last subsection of Section 14.3.2, Oxidative Cleavage of Ketones). In the Baeyer-Villiger rearrangement a carbonyl compound (ketones are almost always used) and an... 

Oxidative cleavage of ketones. Potassium superoxide in combination with Aliquat 336 oxidizes ketones in benzene solution at 20°. Ketones lacking an cf-hydrogen and 1,3-diketones do not react. 

Oxidative cleavage of ketones has been carried out in ligroin at 50-65°< with Caro s acid prepared as described, in a solution conluining more sulfuric acid, less water, and no organic solvent," by refluxing the ketone with a mixture of potassium... 

A similar reagent for the oxidative cleavage of ketones is prepared by cautiously mixing acetic anhydride (65 g.), coned, sulfuric acid (30 g.), and perhydrol (25 g.). Benzophenone (20 g.) added to this solution is converted, after standing for several days at 0°, into phenylbenzoate in nearly quantitative yield. 

Oxidative cleavage of ketones. Levine and Stephens showed that hypohalite oxidation of ketones to acids is not limited to methyl ketones. Thus sodium hypobromite oxidizes propiophenone to benzoic acid in 96% yield, probably as follows ... 

For a review of metal ion-catalyzed oxidative cleavage of alcohols, see Trahanovsky, W.S. Methods Free-Radical Chem. 1973, 4, 133. For a review of the oxidation of aldehydes and ketones, see Verter, H.S. in Zabicky The Chemistry of the Carbonyl Group, pt. 2 Wiley NY, 1970, p. 71. 

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