The products of phosphorylation of N,N-dialkylureas and dialkylcyanamides with phosphorus pentachloride. NMR spectroscopy study

The study by H-1 and P-31 NMR spectroscopy has shown that phosphorylation of N,N-dimethylurea and diethylcyanamide with phosphorus pentachloride results in the formation of N'-(N,N-dialkylchloroformamidino) trichlorophosphonium hexachlorophosphorates where the positive charge of the organyltrichlorophosphonium cation is delocalized over the system of the multiple bonds with participation of the lone electron pair of the nitrogen atom. Bis-N'-(N,N-dialkylchloroformamidino)dichlorophosphonium hexachlorophosphorates, dichlorides of N,N-dialkylchloroformamidinophosphonic and thiophosphonic acids are synthesized where the conjugation of the phosphorus-containing substituent with the chloroformamidinium part of the molecules is retained. Organyltetrachlorophosphoranes based on N,N-dimethylurea and diethylcyanamide exist in polar and nonpolar solvents as orhanyltrichlorophosphonium chlorides.