Baeyer-Villiger Oxidation

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, Synlett2006, 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.2010132, 9236-9239.

General Metal-Free Baeyer-Villiger-Type Synthesis Of Vinyl Acetates
B. Poladura, A. Martínez-Castañeda, H. Rodríguez-Solla, R. Llavona, C. Concellón, V. Del Amo, Org. Lett.201315, 2810-2813.

Enantioselective Baeyer-Villiger Oxidation: Desymmetrization Of Meso Cyclic Ketones And Kinetic Resolution Of Racemic 2-Arylcyclohexanones
L. Zhou, X. H. Liu, J. Ji, Y. H. Zhang, X. L. Hu, L. L. Lin, X. M. Feng, J. Am. Chem. Soc.2012134, 17023-17026.

Asymmetric Baeyer-Villiger Reaction With Hydrogen Peroxide Catalyzed By A Novel Planar-Chiral Bisflavin
S. Murahashi, S. Ono, Y. Imada, Angew. Chem. Int. Ed.200241, 2366-2368.

Conversion Of Cyclic Acetals To Hydroxy Esters By MCPBA Oxidation
J. Y. Kim, H. Rhee, M. Kim, J. Korean Chem. Soc., 200246, 479-483.

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