Davis reagent

Davis reagent
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Names
	IUPAC name 2-(Benzenesulfonyl)-3-phenyloxaziridine
	Other names 2-(Phenylsulfonyl)-3-phenyloxaziridine;
Identifiers
CAS Number	63160-13-4;
3D model (JSmol)	Interactive image;
ChemSpider	283625;
ECHA InfoCard	100.314.396
PubChem CID	320405;
CompTox Dashboard (EPA)	DTXSID10313234 ;
	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−1
Hazards
	GHS labelling:
Pictograms
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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,¹ as well as oxidation of thiols to sulfones.² It is named for Franklin A. Davis.

References

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.
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.

[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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