Oxidation of sulfides to sulfoxides with 3-aryl-2-tert-butyloxaziridines under high pressure

Abstract

3-Phenyl-2-tert-butyloxaziridine has been shown to behave as an oxidant under 800 MPa at 100 °C to oxidize sulfides to sulfoxides, in spite of having been reported to be inactive as an oxidant and to undergo thermal rearrangement to N-tert-butyl-α-phenylnitrone at atmospheric pressure. It has been shown that under thermal and high-pressure conditions the ability of the oxaziridine to react changes dramatically. The mechanism for the high-pressure reaction is also discussed.