Polymer-Supported N-Phenylsulfonyl-oxaziridine: A Versatile Oxidant

Significance

Polymer-supported N-phenylsulfonyloxaziridine was prepared and used for oxidation of sulfide, selenide, and phosphine. Thus, Schiff base condensation of polymer-supported benzaldehyde 1 with benzenesulfinamide under microwave irradiation conditions gave polymer-supported sulfonamide 2. Polymeric sulfonamide 2 was oxidized with MCPBA and potassium hydroxide to give the desired polymeric phenylsulfonyloxaziridine 4 (polymeric Davis reagent). During the reaction polymeric benzsulfoneamide 3 should be generated in situ and underwent oxidation of the C=N unit successively. Oxidation of sulfide 5, selenide 7, and phosphine 9 was carried out with polymeric oxaziridine 4 at room temperature to give the corresponding sulfone 6, enone 8, and phosphine oxide 10 in 98, 83, and 99% yield, respectively.