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Synthesis of Phosphorus-Containing Podands―Analogs of Diglycolamide Based on Diphenyl- and Dibutylphosphorylmethanol under Phase Transfer Catalysis Conditions

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Abstract

A convenient method for preparation of phosphorus-containing podands R2P(O)CH2OCH2X, where X = C(O)NBu2; P(O)R′2, R = R′ = Ph, Bu, R = Ph, R′ = Bu via OH-alkylation of phosphorylmethanols under the phase transfer conditions in the presence of Cs2CO3 was developed. Carbamoyl-substituted dimethyl ethers were synthesized via transformation of phosphorylmethanols to phosphorylmethoxyacetic acids, followed by amidation. Symmetrical bisphosphoryl substituted dimethyl ethers were obtained by reaction of phosphorylmethanols with tosyl chloride in the presence of Cs2CO3. The synthesis of unsymmetrical substituted ether in the presence of Cs2CO3 was complicated by transesterification of phosphorylmethyl tosylate resulting in the formation of symmetrical dimethyl ethers as byproducts.

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Authors and Affiliations

  1. Institute of Chemicals and High Purity Compounds, National Research Center “Kurchatov Institute,”, Bogorodskii val 3, Moscow, 107076, Russia

    A. V. Kharlamov, S. K. Belus & N. A. Bondarenko

  2. Nesmeyanov Institute of Organolement Compounds, Russian Academy of Sciences, Moscow, Russia

    O. I. Artyushin

Authors
  1. A. V. Kharlamov
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  2. S. K. Belus
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  3. O. I. Artyushin
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  4. N. A. Bondarenko
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Corresponding author

Correspondence to N. A. Bondarenko.

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Original Russian Text © A.V. Kharlamov, S.K. Belus, O.I. Artyushin, N.A. Bondarenko, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 9, pp. 1498–1505.

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Kharlamov, A.V., Belus, S.K., Artyushin, O.I. et al. Synthesis of Phosphorus-Containing Podands―Analogs of Diglycolamide Based on Diphenyl- and Dibutylphosphorylmethanol under Phase Transfer Catalysis Conditions. Russ J Gen Chem 88, 1842–1849 (2018). https://doi.org/10.1134/S107036321809013X

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  • DOI: https://doi.org/10.1134/S107036321809013X

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