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

Abstract

A series of new sulfoximine derived bis(fluoroalkyl)phosphoramidates of the type MeRS(O)NP(O)(OR_F)₂ (R = Me or Ph; R_F = 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.

GRAPHICAL ABSTRACT

KEYWORDS:

• Phosphite
• phosphoramidate
• sulfoximine
• fluoroalkyl alcohols
• NMR spectroscopy

Acknowledgements

We are grateful to the Tunisian Ministry of High Education and Scientific Research for financial support (LR99ES14) of this research.

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

This work was supported by Tunisian Ministry of High Education and Scientific Research [grant number (LR99ES14)].