New Organic Derivatives of O,O′-(o-, m-, andp-Ditolyl)/Dibenzyldithiophosphates: Synthesis and Characterization

Abstract

Reactions of (m- and p-ClC ₆ H ₄ NH ₂ ), (p-BrC ₆ H ₄ NO ₂ ), and (p-ClCOC ₆ H ₄ NO ₂ ) with sodium O,O′-ditolyl/dibenzylphosphorodithionates, (ArO) ₂ PS ₂ Na, (Ar = o−, m−, and p−CH ₃ C ₆ H ₄ or –C ₆ H ₅ CH ₂ ) in 1:1 molar ratio in refluxing toluene under anhydrous conditions resulted in the formation of the compounds (ArO) ₂ PS ₂ C ₆ H ₄ L and (ArO) ₂ PS ₂ COC ₆ H ₄ L (L = NH ₂ or NO ₂ ) in 87–94% yield. These viscous compounds were characterized by elemental analyses, molecular weight determination, and IR and NMR ( ¹ H, ¹³ C, and ³¹ P) spectroscopic studies, which revealed a monodentate mode of bonding of the dithiophosphate moiety with the carbon of the phenyl ring of the organic moiety leading to a P–S–C linkage.

Keywords:

• Dithiophosphate
• organophosphorus
• phosphorodithioate
• phosphorus–sulfur

We are grateful to the Central Drug Research Institute, Lucknow, for providing spectral studies.

Notes

∗Hydrogen bonded.