Synthesis and Dynamic NMR Study of a Functionalized Sulfonamide Phosphonate Diester.

Protonation of the highly reactive 1:1 intermediate produced in the reaction between triphenylphosphite and activated acetylene by sulfonamide leads to a phosphonate ylide, which undergoes methanol elimination in the presence of moisture to produce a highly functionalized sulfonamide phosphonate diester. A dynamic nuclear magnetic resonance (NMR) effect is observed in the 1H NMR spectra of this compound as a result of restricted rotation around the single C‒N bond. The coalescence temperature was observed at TC = 352.5 K, and the free energy of activation (ΔG#) for this process is 75.6 ± 2 kJ.mol−1. GRAPHICAL ABSTRACT [ABSTRACT FROM AUTHOR]