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Davis reagent

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(Redirected from Davis oxaziridine)
Davis reagent
Names
IUPAC name 2-(Benzenesulfonyl)-3-phenyloxaziridine
Other names
  • 2-(Phenylsulfonyl)-3-phenyloxaziridine
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.314.396 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C13H11NO3S/c15-18(16,12-9-5-2-6-10-12)14-13(17-14)11-7-3-1-4-8-11/h1-10,13H
SMILES
  • C1=CC=C(C=C1)C2N(O2)S(=O)(=O)C3=CC=CC=C3
Properties
Chemical formula C13H11NO3S
Molar mass 261.30 g·mol
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Davis reagent (3-phenyl-2-(phenylsulfonyl)-1,2-oxaziridine or 2-(benzenesulfonyl)-3-phenyloxaziridine) is a reagent used for oxidation in the Davis oxidation reaction, as well as oxidation of thiols to sulfones. It is named for Franklin A. Davis.

References

  1. Davis, Franklin A.; Vishwakarma, Lal C.; Billmers, Joanne G.; Finn, John (1 August 1984). "Synthesis of α-hydroxycarbonyl compounds (acyloins): direct oxidation of enolates using 2-sulfonyloxaziridines". The Journal of Organic Chemistry. 49 (17): 3241–3243. doi:10.1021/jo00191a048.
  2. Sandrinelli, Franck; Perrio, Stéphane; Beslin, Pierre (13 September 1999). "A New Reaction of 2-(Phenylsulfonyl)-3-phenyloxaziridine (Davis Reagent): Oxidation of Thiolates to Sulfinates. Application to the Synthesis of Sulfones". Organic Letters. 1 (8): 1177–1180. doi:10.1021/ol990170k.
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