Further Information
Literature
Related Reactions
Dakin Reaction
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 hydrogen peroxide 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.
Mechanism of the Baeyer-Villiger Oxidation
Recent Literature
Baeyer-Villiger Oxidation of Ketones to Esters with Sodium Percarbonate/Trifluoroacetic
Acid
G. A. Olah, Q. Wang, N. J. Trivedi, G. K. S. Prakash, Synthesis,
1991, 739-740.
Selenoxides as Catalysts for Epoxidation and Baeyer-Villiger Oxidation with
Hydrogen Peroxide
M. A. Goodman, M. R. Detty, Synlett,
2006, 1100-1104.
Asymmetric Baeyer-Villiger Reaction with Hydrogen Peroxide Catalyzed by a
Novel Planar-Chiral Bisflavin
S. Murahashi, S. Ono, Y. Imada,
Angew. Chem. Int. Ed., 2002, 41,
2366-2368.
Conversion of Cyclic Acetals to Hydroxy Esters by MCPBA Oxidation
J. Y. Kim, H. Rhee, M. Kim, J. Korean Chem. Soc., 2002, 46,
479-483.
