Browsing by Author "Shtamburg, V. V."

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Interaction of N-Alkoxy-N-Chloro-N’-Arylureas With Trialkyl Phosphites as a Route to Dialkyl N-Alkoxy-N-(N’-Arylcarbamoyl)Phosphoramidates. Products Structur
(Ukrainian State University of Science and Technologies, 2026) Shtamburg, Vasiliy G.; Klots, E. A.; Anishchenko, A. A.; Shtamburg, V. V.; Shishkina, S. V.; Mazepa, A. V.; Kravchenko, S. V.
ENG: It is shown that the interaction of N-alkoxy-N-chloro-N’-arylureas with trialkyl phosphites in diethyl ether at room temperature yields dialkyl N-alkoxy-N-(N’-arylcarbamoyl)phosphoramidates. The structures of the dialkyl N-alkoxy-N-(N’-arylcarbamoyl)phosphoramidates were finally confirmed by a single-crystal X-raydiffraction study. The structural peculiarities of dialkyl N-alkoxy-N-(N’-arylcarbamoyl)phosphoramidates are discussed. The single-crystal X-ray diffraction study of dimethyl N-methoxy-N-(N’-4-nitrophenylcarbamoyl)phosphoramidate, dimethyl N-benzyloxy-N-(N’-4-nitrophenylcarbamoyl)phosphoramidate, and diethyl N-methoxy-N-(N’-4-chlorophenylcarbamoyl)phosphoramidate revealed the planar configuration of the N(OR) nitrogen atom. The strong conjugation of the lone pair on the N(OR) nitrogen atom with the π-systems of the P=O and C=O double bonds leads to a planar configuration of the N(OR) nitrogen. Differences in the N–C(=O) carbamoyl bond are observed in dialkyl N-alkoxy-N-(N’-arylcarbamoyl)phosphoramidates. The N(Ar)–C(O) bond is shorter than the N(OR)–C(O) bond; a significant length difference of the N–C(=O) carbamoyl bonds is observed. This phenomenon may be caused by the fact that the conjugation of the lone pair on the N(OR) nitrogen atom with the carbamoyl C=O group is weaker than the conjugation of the lone pair on the N(Ar) nitrogen atom with the same carbamoyl C=O group. In all cases, the N-aryl substituent is almost coplanar with the carbamoyl group.