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拜耳-维利格氧化_Baeyer-Villiger氧化_Baeyer-Villiger Oxidation

Baeyer-Villiger Oxidation  拜耳-维利格氧化



Baeyer-Villiger氧化是羰基附近碳-碳键的氧化断裂,羰基将酮转化为酯,将环酮转化为内酯。Baeyer-Villiger可以用过酸(如MCBPA)或过氧化氢和路易斯酸进行。


反应的区域特异性取决于羰基上取代基的相对迁移能力。能够稳定正电荷的取代基更容易迁移,因此优先顺序为:叔。烷基>环己基>秒。烷基>苯基>普里姆。烷基>CH3。在某些情况下,立体电子或环应变因素也影响区域化学结果。


Baeyer-Villiger氧化机理





相关反应

Dakin反应

Related Reactions

Dakin Reaction





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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