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Diphenyl(N-alkyl-N-diphenylphosphinylmethyl)carbamoylmethylphosphine Oxides: Synthesis and NMR Spectroscopy Study

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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).

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Funding

The work was carried out within the framework of the state task of A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences (no. 075-00697-22-00) with the support of the Ministry of Science and Higher Education of Russia, as well as within the framework of research by the National Research Center “Kurchatov Institute”. The study of the properties of the obtained compounds was carried out using the scientific equipment of the Center for Collective Use of the National Research Center “Kurchatov Institute”–IREA with the financial support of the Ministry of Science and Higher Education of Russia (agreement no. 075-15-2022-1157, 16.08.2022).

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Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991, Moscow, Russia

    O. I. Artyushin

  2. Institute of Chemical Reagents and High Purity Chemical Substances of National Research Centre “Kurchatov Institute”, 107076, Moscow, Russia

    K. V. Tcarkova & N. A. Bondarenko

  3. National Research Center “Kurchatov Institute”, 123098, Moscow, Russia

    K. V. Tcarkova & N. A. Bondarenko

Authors
  1. O. I. Artyushin
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  2. K. V. Tcarkova
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  3. N. A. Bondarenko
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Correspondence to N. A. Bondarenko.

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To the 145th anniversary of A.E. Arbuzov

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Artyushin, O.I., Tcarkova, K.V. & Bondarenko, N.A. Diphenyl(N-alkyl-N-diphenylphosphinylmethyl)carbamoylmethylphosphine Oxides: Synthesis and NMR Spectroscopy Study. Russ J Gen Chem 92, 2598–2606 (2022). https://doi.org/10.1134/S1070363222120076

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