Bayer-Villiger Oxidation Mechanism

Study Notes

Mechanism

The Bayer-Villiger oxidation is a chemical reaction that involves the oxidation of a ketone to an ester using a peroxide, typically a peroxyacid. The mechanism involves the following steps:

Step 1: Formation of the Criegee intermediate

The ketone reacts with the peroxide to form a Criegee intermediate, a highly reactive species that contains a three-membered ring.
The Criegee intermediate is a key intermediate in the Bayer-Villiger oxidation.

Step 2: Migration of the R group

The R group (alkyl or aryl) migrates from the original ketone to the oxygen atom of the peroxide, forming a new bond.
This step is the rate-determining step of the reaction.

Step 3: Formation of the ester

The Criegee intermediate rearranges to form the ester product, with the R group now attached to the oxygen atom.
The ester product is typically formed in high yield and with high selectivity.

Key features of the mechanism

The reaction is highly stereospecific, with the configuration of the starting ketone being retained in the product ester.
The reaction is also highly regioselective, with the R group migrating to the oxygen atom in a predictable manner.
The Bayer-Villiger oxidation is often used in organic synthesis to convert ketones into esters, which can be further transformed into other functional groups.

Description

Learn about the steps involved in the Bayer-Villiger oxidation reaction, including the formation of the Criegee intermediate, migration of the R group, and formation of the ester product. Understand the key features of this stereospecific and regioselective reaction.