Mild and efficient access to lithium alkanesulfinates based on oxaziridine-promoted oxidation of thiolates

Lithium alkanethiolates do not react with N-sulfonyloxaziridine 1 to generate sulfenate species, as uniformly reported in other series. In the present case, a double oxidation reaction is exclusively observed. This unexpected outcome was then exploited for a general, mild and straightforward route to aliphatic sulfinate salts. Investigation of further transformation into sulfones is also described.