Baeyer-Villiger Oxidation

The Baeyer-Villiger Oxidation is the transformation of ketones into esters and cyclic ketones into lactones by the use of peroxyacids.

General features:
1. The reaction tolerates the presence of many functional groups in the ketone.
2. The regiochemistry depends on the migratory capacity of the alkyl groups.
3. A wide range of peroxyacids can be used being mCPBA the most common.

Reaction mechanism:
1. The peroxyacid protonates the oxygen of the ketone
2. The peroxyacid attacks the more electrophile carbonyl carbon
3. Formation of the “Criegee intermediate”
4. One of the substituents from the ketone migrates to the oxygen of the peroxide group.
5. Deprotonation leads to the ester.

Pinterest:
https://www.pinterest.es/pin/67166973...

References:
https://nrochemistry.com/baeyer-villi...

Seminal publication:
Ber. Dtsch. Chem. Ges. 1899, 32, 3625-3633. https://doi.org/10.1002/cber.18990320...

Related reactions in organic chemistry:
Parikh-Doering oxidation: Parikh-Doering Oxidation
Swern oxidation: Swern Oxidation
Ley-Griffith oxidation: Ley-Griffith Oxidation
Corey-Gilman-Ganem oxidation: Corey-Gilman-Ganem Oxidation
Corey-Kim oxidation: Corey-Kim Oxidation

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