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Enethiolates derived from dithioesters were efficiently converted into the corresponding vinylsulfenates by oxidation with a unique N-sulfonyloxaziridine derived from pinacolone is described. S-alkylation of the resulting vinyl sulfenates with an alkyl halide gives ketene dithioacetal S-oxides in good yield.

Aromatic (super 11)C-sulfones were synthesized by S alkylation of lithium arenesulfinates, which are readily available from the corresponding thiols by an oxaziridine-mediated oxidation reaction with [(super 11)C]alkyl iodines in THF/H2O (4:1) at 150 degree Celsius. The radiosyntheses, including purification by HPLC, were completed in an average of 35 min from the end of the bombardment with 55-76% overall radiochemcial yields.

A novel method for the generation and subsequent synthetic application of sulfenate anions is presented. The oxidation reaction, combined with in situ trapping of the sulfenate that is formed, reveals exceptional promise as a convenient approach to the synthesis of sulfoxides. The method is highly competitive with existing repertoire since its advantages include its excellent yields, tolerance of a wide range of substrates, ease of purification and high chemoselectivity.