Davis oxidation
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In organic chemistry, the Davis oxidation or Davis' oxaziridine oxidation refers to oxidations involving the use of the Davis reagent (2-(phenylsulfonyl)-3-phenyloxaziridine) or other similar oxaziridine reagents.[1] This reaction mainly refers to the generation of α-hydroxy carbonyl compounds (acyloins) from ketones or 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]
| Davis oxidation | |
|---|---|
| Named after | Franklin A. Davis |
| Reaction type | Organic redox reaction |
| Identifiers | |
| Organic Chemistry Portal | davis-oxidation |
Other oxidations carried out by Davis' reagent include the oxidation of sulfides and selenides to sulfoxides[5][6] and selenoxides[7] without further oxidation; the oxidation of alkenes to epoxides;[8][9][10] and the oxidation of amines to hydroxylamines and amine oxides.[11]
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
- Rubottom oxidation - also produces α-hydroxy carbonyl compounds
References
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