Davis oxidation

{{Reactionbox

| Name = Davis oxidation

| Type = Organic redox reaction

| NamedAfter = Franklin A. Davis

| Section3 = {{Reactionbox Identifiers

| OrganicChemistryNamed = davis-oxidation

}}

}}

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.{{cite book |last1=Kürti |first1=László |last2=Czakó |first2=Barbara |title=Strategic Applications of Named Reactions in Organic Synthesis |date=29 September 2005 |isbn=978-0-12-429785-2 |pages=130–131|publisher=Elsevier Science }} This reaction mainly refers to the generation of α-hydroxy carbonyl compounds (acyloins) from ketones or esters.{{cite journal |last1=Davis|first1=Franklin A.|author-link1=Franklin A. Davis|last2=Vishwakarma |first2=Lal C.|last3=Billmers|first3=Joanne G.|last4=Finn|first4=John|date=1 August 1984|title=Synthesis of α-hydroxycarbonyl compounds (acyloins): direct oxidation of enolates using 2-sulfonyloxaziridines|url= |journal=The Journal of Organic Chemistry|volume=49|issue=17|pages=3241–3243|doi=10.1021/jo00191a048|access-date=}}{{cite journal |last1=Davis |first1=Franklin A. |last2=Chen |first2=Bang Chi |author1-link=Franklin A. Davis |title=Asymmetric hydroxylation of enolates with N-sulfonyloxaziridines |journal=Chemical Reviews |date=1992 |volume=92 |issue=5 |pages=919–934 |doi=10.1021/cr00013a008}} 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.{{cite journal |last1=Evans |first1=David Albert |last2=Morrissey |first2=Michael M. |last3=Dorow |first3=Roberta L. |author1-link=David A. Evans |title=Asymmetric oxygenation of chiral imide enolates. A general approach to the synthesis of enantiomerically pure α-hydroxy carboxylic acid synthons |journal=Journal of the American Chemical Society |date=1985-07-01 |volume=107 |issue=14 |pages=4346–4348 |doi=10.1021/ja00300a054}}

Other oxidations carried out by Davis' reagent include the oxidation of sulfides and selenides to sulfoxides{{cite journal |last1=Mata |first1=Ernesto G. |title=Recent advances in the synthesis of sulfoxides from sulfides |journal=Phosphorus, Sulfur, and Silicon and the Related Elements |date=1996 |volume=117 |issue=1 |pages=231–286 |doi=10.1080/10426509608038790}}{{cite journal |last1=Bohé |first1=Luis |last2=Lusinchi |first2=Marie |last3=Lusinchi |first3=Xavier |title=Oxygen atom transfer from a chiral N-alkyl oxaziridine promoted by acid. The asymmetric oxidation of sulfides to sulfoxides |journal=Tetrahedron |date=1999 |volume=55 |issue=1 |pages=155–156 |doi=10.1016/S0040-4020(98)01035-7}} and selenoxides{{cite journal |last1=Davis |first1=Franklin A. |last2=Stringer |first2=Orum D. |last3=Billmers |first3=Joanne M. |author1-link=Franklin A. Davis |title=Oxidation of selenides to selenoxides using 2-sulfonyloxaziridines |journal=Tetrahedron Letters |date=1983 |volume=24 |issue=12 |pages=1213–1216 |doi=10.1016/S0040-4039(00)81617-2}} without further oxidation; the oxidation of alkenes to epoxides;{{cite journal |last1=Davis |first1=Franklin A. |last2=Abdul-Malik |first2=Nadia F. |last3=Awad |first3=Sami B. |last4=Harakal |first4=Mark E. |author1-link=Franklin A. Davis |title=Epoxidation of olefins by oxaziridines |journal=Tetrahedron Letters |date=1981 |volume=22 |issue=10 |pages=917–920 |doi=10.1016/0040-4039(81)89008-9}}{{cite journal |last1=Davis |first1=Franklin A. |last2=Harakal |first2=Mark E. |last3=Awad |first3=Sami B. |title=Chemistry of oxaziridines. 4. Asymmetric epoxidation of unfunctionalized alkenes using chiral 2-sulfonyloxaziridines: evidence for a planar transition state geometry |journal=Journal of the American Chemical Society |date=1983 |volume=105 |issue=10 |pages=3123–3126 |doi=10.1021/ja00348a029}}{{cite journal |last1=Bohé |first1=Luis |last2=Lusinchi |first2=Marie |last3=Lusinchi |first3=Xavier |title=Oxygen atom transfer from a chiral oxaziridinium salt. Asymmetric epoxidation of unfunctionalized olefins |journal=Tetrahedron |date=1999 |volume=55 |issue=1 |pages=141–154 |doi=10.1016/S0040-4020(98)01034-5}} and the oxidation of amines to hydroxylamines and amine oxides.{{cite journal |last1=Zajac |first1=Walter W. Jr. |last2=Walters |first2=Thomas R. |last3=Darcy |first3=Michael G. |title=Oxidation of amines with 2-sulfonyloxaziridines (Davis' reagents) |journal=The Journal of Organic Chemistry |date=1988 |volume=53 |issue=25 |pages=5856–5860 |doi=10.1021/jo00260a012}}