Dakin oxidation

The Dakin oxidation is most commonly used to synthesize benzenediols and alkoxyphenols.

The Dakin oxidation can occur in mild acidic conditions as well, with a mechanism analogous to the base-catalyzed mechanism.

The Dakin oxidation starts with nucleophilic addition of a hydroperoxide anion to the carbonyl carbon, forming a tetrahedral intermediate (2).

The Dakin oxidation has two rate-limiting steps: nucleophilic addition of hydroperoxide to the carbonyl carbon and [1,2]-aryl migration.

In addition, the Dakin oxidation is useful in the synthesis of indolequinones, naturally-occurring compounds that exhibit high anti-biotic, anti-fungal, and anti-tumor activities.

Using an ionic liquid solvent with catalytic methyltrioxorhenium (MTO) dramatically accelerates Dakin oxidation.

Adding dry UHC to solventless phenyl aldehyde or ketone also accelerates Dakin oxidation.

The Dakin oxidation, which is closely related to the Baeyer-Villiger oxidation, is not to be confused with the Dakin-West reaction, though both are named after Henry Drysdale Dakin.

The Dakin oxidation is an organic redox reaction in which an ortho- or para-hydroxylated phenyl aldehyde or ketone reacts with hydrogen peroxide in base to form a benzenediol and a carboxylate.