Selective sulfur oxygenation in phosphoroamidate, thionophosphate, and thiophosphate agrochemicals by perfluoro-cis-2,3-dialkyloxaziridine

Several organophosphorus agrochemicals 2a-g with thioether, phosphoramidic, phosphorothioic, and phosphorothionic functions were reacted with perfluoro cis-2-n-butyl-3-n-propyloxaziridine 1. The selective oxygenation of sulfide function to give sulfoxide derivatives 3a-g occurred in high yields without overoxidation to sulfone products. Sulfoxides 3a-e were further oxidized under mild conditions to the corresponding sulfones 4a-e. All the products are themselves of interest as analytical environmental standards and their preparation is described in detail.