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Baeyer-Villiger oxidation

Baeyer-Villiger oxidation is the oxidation of a ketone to a carboxylic acid ester using a peroxyacid as the oxidizing agent. eg. 1:

 

 

eg. 2:

Mechanism

When the two ligands on the carbonyl carbon in the ketone are different, Baeyer-Villiger oxidation is regioselective. Of the two alpha carbons in the ketone, the one that can stabilize a positive charge more effectively, which is the more highly substituted one, migrates from carbon to oxygen preferentially.

eg. 1:

eg. 2:

References

  1. 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.
  2. Baeyer, A.; Villiger, V. Ber. Dtsch. Chem. Ges. 1899, 32, 3625–3633.
  3. P. A. S. Smith in Molecular Rearrangements Part 1, P. de Mayo, Ed. (Wiley- Interscience, New York, 1963) pp 577-591; J. B. Lee, B. C. Uff, Quart. Rev. Chem. Soc. 21, 429-457 (1967);
  4. C. H. Hassall, Org. React. 9,73 (1957); G. R. Krow,ibid. 43, 251-798 (1993);
  5. C. H. Hassall,, Comp. Org. Syn. 7, 671-688 (1991).