Synthesis and characterization of new bis(fluoroalkyl) phosphoramidates bearing sulfoximine groups

A series of new sulfoximine derived bis(fluoroalkyl)phosphoramidates of the type MeRS(O)NP(O)(ORF)2 (R = Me or Ph; RF = CH2CF3, CH2C2F5, CH(CF3)2, CH2CH2C6F13 or CH2CH2C8F17) have been synthesized from phosphoramidation reaction of sulfoximine with bis(polyfluoroalkyl)phosphites as phosphorylating agents. These fluoroalkyl phosphoramidates were characterized by multinuclear (1H, 13C, 19F and 31P) NMR, IR and elemental analyses. Different literature methods were examined; results showed that whilst the presence of fluoroalkoxy groups gave better reactivity than non fluorinated analogs in such reactions, the choice of the method for phosphoramidate formation depended upon the nature of both sulfoximine and fluoroalkoxy groups.