Baeyer–Villiger oxidation
| Baeyer-Villiger oxidation | |
|---|---|
| Named after | Adolf von Baeyer Victor Villiger |
| Reaction type | Organic redox reaction |
| Identifiers | |
| Organic Chemistry Portal | baeyer-villiger-oxidation |
| RSC ontology ID | RXNO:0000031 |
The Baeyer–Villiger oxidation is an organic reaction that forms an ester from a ketone or a lactone from a cyclic ketone, using peroxyacids or peroxides as the oxidant.[1] The reaction is named after Adolf von Baeyer and Victor Villiger who first reported the reaction in 1899.[1]
Reaction mechanism[]
In the first step of the reaction mechanism, the peroxyacid protonates the oxygen of the carbonyl group.[1] This makes the carbonyl group more susceptible to be attacked by the peroxyacid.[1] Next, the peroxyacid attacks the carbon of the carbonyl group forming what is known as the Criegee intermediate.[1] Through a concerted mechanism, one of the substituents on the ketone group migrates to the oxygen of the peroxide group while a carboxylic acid leaves.[1] This migration step is thought to be the rate determining step.[2] Finally, deprotonation of the oxocarbenium ion produces the ester.[1]
The products of the Baeyer–Villiger oxidation are believed to be controlled through both primary and secondary stereoelectronic effects.[3] The primary stereoelectronic effect in the Baeyer–Villiger oxidation refers to the necessity of the oxygen-oxygen bond in the peroxide group to be antiperiplanar to the group that migrates.[3] This orientation facilitates optimum overlap of the