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Baeyer−Villiger Oxidation

Detail Reaction of Baeyer-Villiger Oxidation

Baeyer-Villiger Oxidation involves the oxidation of ketones to esters by the treatment with peroxyacids.

Baeyer−Villiger Oxidation

Cyclic ketones are converted to lactones with ring expansion.

Baeyer−Villiger Oxidation

The overall reaction is an insertion of oxygen atom between the carbonyl group and the adjacent carbon atom in ketone. It involves the migration of a group from carbon to the electron−deficient oxygen. Organic solvents (inert) are used such as glacial acetic acid or chloroform, which can dissolve the reactant.

Baeyer-Villiger Oxidation Mechanism

First of all the peroxyacid protonates the ketone and then peroxyacids undergoes nucleophilic attack on this protonated ketone to form an peroxide intermediate (A). This intermediate then undergoes loss of carboxylate anion and migration of a group from carbon to electron deficient oxygen to yield the protonated ester (B). This finally losses a proton to give an ester.

Baeyer−Villiger Oxidation

Application of group in Baeyer-Villiger Oxidation

The presence of electron releasing groups in the ketone and electron withdrawing groups in the peroxyacids increases the rate of reaction. In unsymmetrical ketones that group migrates which is more electron releasing, thus the migratory aptitude of alkyl groups is in the order 3° > 2° > 1° > CH3.

Electron releasing substituents in the aryl group facilitate migration. The migratory order of aryl groups is p−anisyl > p−tolyl > phenyl > p−chlorophenyl > p−nitrophenol.

In case of alkyl aryl ketones, it is the aryl group which migrates (except in case of tert butyl groups).

Example of Baeyer−Villiger Oxidation

Baeyer−Villiger Oxidation

Baeyer−Villiger Oxidation example

List of Name Reaction of Organic Chemistry consist of detail Reaction Mechanism of all name reactions of Organic Chemistry.

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