Organoselenium-Catalyzed Baeyer-Villiger Oxidation of α,β-Unsaturated Ketones by Hydrogen Peroxide to Access Vinyl Esters

2015 ◽  
Vol 357 (5) ◽  
pp. 955-960 ◽  
Author(s):  
Xu Zhang ◽  
Jianqing Ye ◽  
Lei Yu ◽  
Xinkang Shi ◽  
Ming Zhang ◽  
...  
Keyword(s):  
Hydrogen Peroxide ◽  
Vinyl Esters ◽  
Unsaturated Ketones ◽  
Villiger Oxidation

ChemInform Abstract: Organoselenium-Catalyzed Baeyer-Villiger Oxidation of α,β-Unsaturated Ketones by Hydrogen Peroxide to Access Vinyl Esters.

ChemInform ◽  
2015 ◽  
Vol 46 (29) ◽  
pp. no-no
Author(s):  
Xu Zhang ◽  
Jianqing Ye ◽  
Lei Yu ◽  
Xinkang Shi ◽  
Ming Zhang ◽  
...  
Keyword(s):  
Hydrogen Peroxide ◽  
Vinyl Esters ◽  
Unsaturated Ketones ◽  
Villiger Oxidation

Synthetic application of cyclobutanes V. α-Carbalkoxymethylation of α, β-unsaturated ketones

1977 ◽  
Vol 55 (5) ◽  
pp. 822-830 ◽  
Author(s):  
Hsing-Jang Liu ◽  
Patrick Chi-Lin Yao
Keyword(s):  
Hydrogen Peroxide ◽  
Acetic Acid ◽  
Acetic Anhydride ◽  
Potassium Carbonate ◽  
Alkyl Iodide ◽  
Keto Ester ◽  
Unsaturated Ketones ◽  
Synthetic Application ◽  
Hydrolysis Of ◽  
Villiger Oxidation

Two general methods for α-carbalkoxymethylation of both enolizable and nonenolizable (towards the γ-position) α,β-unsaturated ketones have been developed. Method A involves three synthetic steps: photocycloaddition of the starting enone to 1,1-dimethoxyethylene, hydrolysis–oxidation of the adduct with acetic acid and 30% hydrogen peroxide, and O-alkylation of the resulting mixture of lactone and acid using anhydrous potassium carbonate and an alkyl iodide, e.g., 13 → 17 → 21 + 22 → 23. Method B differs from method A in the means of securing the required cyclobutanone intermediate. Thus, photocycloaddition of 13 to vinyl acetate followed by hydrolysis of the adduct gave two epimeric keto alcohols 39 whose oxidation with dimethyl sulfoxide and acetic anhydride afforded diketone 40. Baeyer–Villiger oxidation of 40 followed by methylation of the products 21 and 22 completed the overall α-carbomethoxymethylation process to give keto ester 23.

Metal hydroxides as catalysts for the Baeyer-Villiger oxidation of cyclohexanone with hydrogen peroxide

2007 ◽  
Vol 90 (2) ◽  
pp. 309-313 ◽  
Author(s):  
Rafael Llamas ◽  
César Jiménez-Sanchidrián ◽  
José Rafael Ruiz
Keyword(s):  
Hydrogen Peroxide ◽  
Metal Hydroxides ◽  
Villiger Oxidation

Hydrotalcites as catalysts for the Baeyer–Villiger oxidation of cyclic ketones with hydrogen peroxide/benzonitrile

Tetrahedron ◽  
2006 ◽  
Vol 62 (50) ◽  
pp. 11697-11703 ◽  
Author(s):  
José Rafael Ruiz ◽  
César Jiménez-Sanchidrián ◽  
Rafael Llamas
Keyword(s):  
Hydrogen Peroxide ◽  
Cyclic Ketones ◽  
Villiger Oxidation

Baeyer–Villiger Oxidation of Cyclohexanone by Hydrogen Peroxide with Fe3O4@GO as Catalyst Under Solvent Free Conditions

2019 ◽  
Vol 149 (7) ◽  
pp. 1765-1771 ◽  
Author(s):  
Guansheng Xiao ◽  
Xi Gao ◽  
Weiting Yan ◽  
Tao Wu ◽  
Xinhua Peng
Keyword(s):  
Hydrogen Peroxide ◽  
Solvent Free ◽  
Solvent Free Conditions ◽  
Villiger Oxidation

Epoxidation and Baeyer–Villiger oxidation using hydrogen peroxide and a lipase dissolved in ionic liquids

2011 ◽  
Vol 13 (8) ◽  
pp. 2154 ◽  
Author(s):  
Aleksandra J. Kotlewska ◽  
Fred van Rantwijk ◽  
Roger A. Sheldon ◽  
Isabel W. C. E. Arends
Keyword(s):  
Hydrogen Peroxide ◽  
Ionic Liquids ◽  
Villiger Oxidation
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