Saturday, 14 December 2013

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]
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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.

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References:

1.
Baeyer, A.; Villiger, V. Ber. Dtsch. Chem. Ges. 1899, 32, 3625–3633.
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