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.
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.
Hypervalent λ3-Bromane Strategy for Baeyer-Villiger Oxidation:
Selective Transformation of Primary Aliphatic and Aromatic Aldehydes to
Formates, Which is Missing in the Classical Baeyer-Villiger Oxidation
Y. Yoshida, K. Murakami, H. Yorimitsu, K. Oshima, J. Am. Chem. Soc., 2010,
132, 9236-9239.
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.
