Dear student,

Baeyer-Villiger Oxidation

The Baeyer-Villiger Oxidation is the oxidative cleavage of a carbon-carbon bond adjacent to a carbonyl, which converts ketones to esters and cyclic ketones to lactones. The Baeyer-Villiger can be carried out with peracids, such as MCBPA, or with H2O2 and a Lewis acid.

The regiospecificity of the reaction depends on the relative migratory ability of the substituents attached to the carbonyl. Substituents which are able to stabilize a positive charge migrate more readily, so that the order of preference is: tert. alkyl > cyclohexyl > sec. alkyl > phenyl > prim. alkyl > CH₃. In some cases, stereoelectronic or ring strain factors also affect the regiochemical outcome.

The reaction of aldehydes preferably gives formates, but sometimes only the liberated alcohol may be isolated due to the solvolytic instability of the product formate under the reaction conditions.

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