Synthesis and structural Studies of phosphonothioamidates

GRAPHICAL ABSTRACT

Abstract

The reaction of isothiocyanates with dialkylphosphites in the presence of strong base yielded the phosphonothioamides 2. Treatment of 2 with methyl iodide afforded the corresponding thioimidates 3 with high yields. All compounds were characterized on the basis of their IR, NMR Spectroscopy (¹H, ¹³C, ¹⁹F, and ³¹P) and in some cases by elemental analysis, HRMS data, and calculations using Density Functional Theory (DFT)-B3LYP//6-311G** and evolution study by ³¹P-NMR in an external lock with D₂O. The conformational molecular structure of compounds 2d and 2f were determined by single-crystal X-ray diffraction analysis.

Keywords:

• Phosphonothioamidates
• phosphonatesthioimidates
• X-ray
• DFT