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A New Reaction of 2-(Phenylsulfonyl)-3-phenyloxaziridine (Davis Reagent):  Oxidation of Thiolates to Sulfinates. Application to the Synthesis of Sulfones

Franck Sandrinelli, Stéphane Perrio* and Pierre Beslin

*Laboratoire de Chimie Moléculaire et Thio-organique (Associé au CNRS, UMR 6507), ISMRA-Université de Caen, 6 boulevard du Maréchal Juin, F-14050 Caen, France, Email:

F. Sandrinelli, S. Perrio, P. Beslin, Org. Lett., 1999, 1, 1107-1109.

DOI: 10.1021/ol990170k

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2-(Phenylsulfonyl)-3-phenyloxaziridine, commonly known as the Davis reagent, enables a generation of sulfinate anions by oxidation of the corresponding thiolates. Subsequent S-alkylation of the sulfinates under phase-transfer catalysis affords sulfones in very good isolated yields.

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Key Words

Davis reagent, alkyl sulfones, oxidation

ID: J54-Y1999