Davis oxidation

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Davis oxidation
Named after Franklin A. Davis
Reaction type Organic redox reaction
Identifiers
Organic Chemistry Portal davis-oxidation

In

esters.[2][3] The reaction is carried out in a basic environment to generate the corresponding enolate from the ketone or ester. This reaction has been shown to work for amides.[4]

Other oxidations carried out by Davis' reagent include the oxidation of

Mechanism

Regarding the α-hydroxylation of carbonyls, the base first converts the ketone or ester into its corresponding enolate. Then, the enolate anion as a nucleophile attacks the oxygen atom of the oxaziridine in a SN2 mechanism, forming a hemiaminal intermediate. The intermediate then fragments into a sulfinimine, and, after protonation, the desired α-hydroxyketone or α-hydroxyester.[3][12][13]

See also

References