Baeyer-Villiger Reaction

 

Definition:

The oxidation of ketones to esters or lactones by peracids.

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Frequency of appearance:

        This bar graph represents all of the online articles that were found to contain this specific name reaction in the title of the article. Tetrahedron letters, Tetrahedron, Synthetic letters, Synthesis, Journal of Organic Chemistry and Journal of the American Chemical Society are represented here. This table by no means represents the periodicity of the name reaction found in the literature.

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Original Reference:

  1. Baeyer, A.; Villiger, V. Ber., 24, 3625 (1899).
  2. Baeyer, A.; Villiger, V. Ber., 33, 858 (1900).

 

Recent academic references: Click here for more references

 

  1. Synthesis of Indolizidines and Pyrrolizidines through the [2 + 2]Cycloaddition of Five-Membered Endocyclic Enecarbamates to Alkyl Ketenes. Unusual Regioselectivity of Baeyer-Villiger Ring Expansions of Alkyl Aza-Bicyclic Cyclobutanones
  • de Faria, A. R.; Salvador, E. L.; Correia, C. R. D.;
    J. Org. Chem.; 2002; 67(11); 3651-3661.             
  1. Synthesis of Medium Ring Ethers. 5. The Synthesis of (+)-Laurencin
  • Burton, J.W., et al., Am.Chem. Soc, 119, 7483-7498, (1997).

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  1. Halogens halt aromatic group migration in Baeyer¯Villiger oxidation
  • Adejare, A., et al., Journal of Fluorine Chemistry, Volume 105, Issue 1, 1 July 2000, Pages 107-109
  1. http://www.chem.wayne.edu/acs-organic-division/essays_2001/wrobleski.pdf

 

Recent process references:

  1. Baeyer-Villiger Oxidation of 5-endo-(Biphenyl-4-ylmethoxy)-7-anti-piperidinobicyclo[2.2.1]heptan-2-one: Process Development and Scale-Up
  • Coleman, M. J.; Crookes, D. L.; Hill, M. L.; Singh, H.; Marshall, D. R.; Wallis, C. J.; Org. Process Res. Dev.;1997; 1(1); 20-25.

 

Mechanism: http://library.tedankara.k12.tr/chemistry/vol5/Breaking and connecting carbon chains/o63.htm

                       

Scope and limitations:

 

Synonyms:

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