Davis oxidation
Davis oxidation | |
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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
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
- ISBN 978-0-12-429785-2.
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