Uses
Davis Oxaziridine is an oxidizing agent used in the preparation of wide variety of pharmaceutical compounds.
Uses
3-Phenyl-2-(phenylsulfonyl)-1,2-oxaziridine, is an oxidizing agent used in the preparation of wide variety of pharmaceutical compounds.
Preparation
3-PHENYL-2-(PHENYLSULFONYL)-1,2-OXAZIRIDINE can be readily prepared on a 100 g scale in 88% yield via
oxidation of N-benzylidenebenzenesulfonamide with buffered m-Chloroperbenzoic Acid or more
conveniently with Potassium Monoperoxysulfate (Oxone). This Baeyer-Villiger type of oxidation of
sulfonimine affords only the trans-oxaziridine. A number of other (±)-trans-2-(arylsulfonyl)-3-
aryloxaziridines (2) can also be prepared by these methods.
General Description
3-PHENYL-2-(PHENYLSULFONYL)-1,2-OXAZIRIDINE is a neutral, aprotic, electrophilic oxidizing agent for the chemoselective oxidation of many nucleophilic
substrates
[1].
storage
3-Phenyl-2-(phenylsulfonyl)-1,2-oxaziridine can be stored in a brown bottle in the refrigerator for years without
noticeable decomposition. Storage at rt for long periods of time, however, is potentially hazardous.
[2] The nitro-substituted oxaziridines (2) are more thermally stable and are recommended for reactions at elevated
temperatures.
References
1. (a) Davis, F. A.; Sherppard, A. C. T 1989, 45, 5703. (b) Davis, F. A.; Chen, B.-C. CRV 1992, 92, 912.
2. Vishwakarma, L. C.; Stringer, O. D.; Davis, F. A. OS 1988, 66, 203.
