Education is the most powerful weapon,We Can Use to Change the World- Nelson Mandela

Baeyer-Villiger oxidation


Baeyer-Villiger oxidation

Also known as: Baeyer-Villiger rearrangement

Schematic of the Baeyer-Villiger oxidation. Reagents: ketone, peroxyacid. Product: ester. Comments: The more electron rich group migrates to the oxygen.
The Baeyer-Villiger oxidation is an organic reaction used to convert a ketone to an ester using a peroxyacid (such as mCPBA). The reaction of the ketone with the acid results in a tetrahedral intermediate, with an alkyl migration following to release a carboxylic acid. The more electron rich R group migrates to the oxygen in this concerted process, allowing for accurate prediction of the stereochemistry of the product.[1]

Mechanism

Mechanism of the Baeyer-Villiger oxidation. Attack with another molecule of peroxyacid followed by deprotonation. As a positive charge is forming on the labeled oxygen (as the carbonyl group abstracts a proton from the acid), the more electron rich R group migrates to the oxygen to stabilize it.

No comments:

Post a Comment

Subscribe to: Posts (Atom)