Polymer‐Supported N‐Phenylsulfonyloxaziridine (Davis Reagent): A Versatile Oxidant

Abstract

An efficient preparation of a new recyclable polymer-supported oxidizing agent based on Nphenylsulfonyloxaziridine has been developed. This new polymer-supported oxidant was shown to effect a clean and selective conversion of a range of sulfides, selenides, amines, phosphines and enolates to the corresponding sulfoxides, selenoxides, N-oxides, phosphine oxides and a-hydroxy carbonyl compounds. It also enabled tetrahydrobenzimidazoles to be oxidatively rearranged to spiro-fused 5-imidazolones. Recycling of the polymer-supported oxidant is possible with minimal loss of activity after several reoxidations.

7.07 α-Oxygenation of Carbonyl Compounds

“…3c The use of polymer-supported Davis reagent gives a cleaner reaction and facile recycling of the resulting sulfonylimine. 62 …”

7.28 Oxidation of Sulfur, Selenium, and Tellurium

“…Soluble and recyclable polymer-supported N-benzenesulfonyl-3-phenyloxaziridine has been prepared and used in the oxidation of selenides, followed by b-elimination to alkenes. 338 Oxidative addition of halogens (Cl 2 , Br 2 , I 2 ) to selenides 89 is an old reaction (Scheme 46, equation 18 The halogenation/hydrolysis/elimination procedure has been applied as an alternative approach to that reported in Scheme 40 (equation 15) for the synthesis of functionalized alkenes. 342 Diaryl and aryl benzyl selenides are oxidized with PhICl 2 at À 40 1C in aqueous pyridine to selenoxides.…”

Oxidation reactions using polymer-supported 2-benzenesulfonyl-3-(4-nitrophenyl)oxaziridine

“…3,7e10 Amongst them, a number of oxidants, such as IBX, 11 trimethylamine N-oxide, 12 dichromate, 13 and Swern oxidants 14,15 have been developed. 16 Although polymer 1 effected clean and selective oxidation with high yields and simple workup, it was not thermally stable and could only be applied to reactions at ambient or low temperatures. 1) and its application to the oxidation of sulfides, selenides, amines, phosphines, and enolates.…”