Davis reagent

CAS 63160-13-4, Cat. No EN300-175119

Reagent for the chemoselective oxidation of many nucleophilic substrates

The Davis reagent, also known as the Davis Oxaziridine, is a versatile and powerful reagent commonly used for the oxidation of various sulfur-containing compounds. It is specifically known for its ability to oxidize sulfides to sulfoxides selectively, without over-oxidation to sulfones. The reagent is a white solid that soluble in DCM, CHCl₃, and THF but insoluble in hexane, pentane, and water. Thiols are oxidized to sulfenic acids which can then be trapped by alkynes to give vinyl sulfoxides. Oxidation of thiones gives thione S-oxides which may undergo desulfurization to ketone.

Synonyms: 2-(Phenylsulfonyl)-3-phenyloxaziridine, 2-Benzenesulfonyl-3-phenyloxaziridine, 3-Phenyl-2-(phenylsulfonyl)-1,2-oxaziridine, 3-Phenyl-2-phenylsulfonyloxaziridine, 3-Phenyl-N-phenylsulfonyloxaziridine, N-(Phenylsulfonyl)phenyloxaziridine, N-Benzenesulfonyl-3-phenyloxaziridine

Selected publication

1. (±)-Trans-2-(Phenylsulfonyl)-3-Phenyloxaziridine.

Chen B.-C.; Davis F. A. Encyclopedia of Reagents for Organic Synthesis 2001. DOI: 10.1002/047084289X.rp115