Diphenyl(N-alkyl-N-diphenylphosphinylmethyl)carbamoylmethylphosphine Oxides: Synthesis and NMR Spectroscopy Study
O. I. Artyushina (https://orcid.org/0000-0001-6333-5973), K. V. Tcarkovab, c (https://orcid.org/0000-0001-8730-0521), and N. A. Bondarenkob, c, * (https://orcid.org/0000-0002-6704-6957)
aA. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, 119991 Russia
bInstitute of Chemical Reagents and High Purity Chemical Substances of National Research Centre “Kurchatov Institute”, Moscow, 107076 Russia
cNational Research Center “Kurchatov Institute”, Moscow, 123098 Russia
email: *bond039@mail.ru
Received 5 October, 2022
Abstract—
Modified tridentate carbamoylmethylphosphine oxides Ph2P(O)CH2N(R)CH2P(O)Ph2 (R = Et, i-Pr, Bu, Oct) were synthesized by the reaction of phosphorylated amines Ph2P(O)CH2NHR (R = Et, i-Pr, Bu, Oct) with diphenylphosphinylacetic acid in the presence of diisopropylcarbodiimide or by reacting with diphenylphosphinylacetyl chloride. According to the 1H, 13C{1H}, 31P{1H} NMR spectroscopy data, in CDCl3 solutions, the modified carbamoylmethylphosphine oxides exist in two conformers in the ratio of approximately 1.3:1 (R = Et), 1.5 : 1 (R = i-Pr) or 1 : 1 (R = Bu, Oct).
Keywords:
carbamoylmethylphosphine oxides,
N-alkyl-N-(diphenylphosphinylmethyl)amines,
amidation,
diphenylphosphinylacetic acid,
diisopropylcarbodiimide,
N-alkyl-N-(diphenylphosphinylmethyl)diphenylphosphinylacetamides
DOI: 10.1134/S1070363222120076