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New Tridentate Carbamoylmethylphosphine Oxides: Synthesis and NMR Spectra

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Abstract

Amidation of diphenylphosphorylacetic acid gave tridentate ligands Ph2P(O)CH2CON(R)· CH2CH2P(O)Ph2 (R = Me, Bu, Oct) containing a phosphoryl group in the amide moiety. According to the 1H, 13C{1H}, and 31P{1H} NMR spectra, the synthesized compounds exist in CDCl3 solution as two conformers at the ratios of ~2.5 : 1 (R = Me), 2.6 : 1 (R = Bu), and 3.0:1 (R = Oct). These ratios do not change with temperature (heating or cooling).

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REFERENCES

  1. Rozen, A.M. and Krupnov, B.V., Russ. Chem. Rev., 1996, vol. 65, no. 11, p. 973. https://doi.org/10.1070/RC1996v065n11ABEH000241

    Article  Google Scholar 

  2. Mastryukova, T.A., Artyushin, O.I., Odinets, I.L., and Tananaev, I.G., Ross. Khim. Zh., 2005, vol. 49, no. 2, p. 86.

    CAS  Google Scholar 

  3. Sharova, E.V., Artyushin, O.I., and Odinets, I.L., Russ. Chem. Rev., 2014, vol. 83, no. 2, p. 95. https://doi.org/10.1070/RC2014v083n02ABEH004384

    Article  CAS  Google Scholar 

  4. Artyushin, O.I., Sharova, E.V., Odinets, I.L., Lysenko, K.A., Golovanov, D.G., Mastryukova, T.A., Pribylova, G.V., Tananaev, I.G., and Myasoedova, G.V., Russ. Chem. Bull., Int. Ed., 2006, vol. 55, no. 8, p. 1440. https://doi.org/10.1007/s11172-006-0437-2

    Article  CAS  Google Scholar 

  5. Bondarenko, N.A., Kharlamov, A.V., and Vendilo, A.G., Russ. Chem. Bull., Int. Ed., 2009, vol. 58, no. 9, p. 1872. https://doi.org/10.1007/s11172-009-0256-3

    Article  CAS  Google Scholar 

  6. Evreinov, V.I., Safronova, Z.V., Yarkevich, A.N., Kharitonov, A.V., Bondarenko, N.A., and Tsvetkov, E.N., Russ. J. Gen. Chem., 1999, vol. 69, no. 7, p. 1047.

    CAS  Google Scholar 

  7. Shvetsov, I.K., Trukhlyaev, P.S., Kalistratov, V.A., Kulazhko, V.G., Kharitonov, A.V., Antoshin, A.E., and Tsvetkov, E.N., Radiokhimiya, 1989, vol. 3, no. 2, p. 63.

    Google Scholar 

  8. Bondarenko, N.A., Russ. J. Gen. Chem., 1999, vol. 69, no. 7, p. 1016.

    CAS  Google Scholar 

  9. Turanov, A.N., Karandashev, V.K., Kharitonov, A.V., Lezhnev, A.N., Safronova, Z.V., Yarkevich, A.N., and Tsvetkov, E.N., Russ. J. Gen. Chem., 1999, vol. 69, no. 7, p. 1068.

    CAS  Google Scholar 

  10. Rahman, M.S., Steed, J.W., and Hii, R.R., Synthesis, 2000, vol. 2000, no. 9, p. 1320. https://doi.org/10.1055/s-2000-6422

    Article  Google Scholar 

  11. Matveeva, E.V., Petrovskii, P.V., Klemenkova, Z.S., Bondarenko, N.A., and Odinets, I.L., C. R. Chim., 2010, vol. 13, nos. 8–9, p. 964. https://doi.org/10.1016/j.crci.2010.03.005

    Article  CAS  Google Scholar 

  12. Yarkevich, A.N., Petrova, L.N., and Bachurin, S.O., Russ. J. Gen. Chem., 2012, vol. 82, no. 10, p 1659. https://doi.org/10.1134/S1070363212100052

  13. Gordon, A.J. and Ford, R.A., The Chemistʼs Companion: A Handbook of Practical Data, Techniques, and References, New York: Wiley, 1972.

  14. Petrov, E.S., Tsvetkov, E.N., Terekhova, M.I., Malevannaya, R.A., Shatenshtein, A.I., and Kabachnik, M.I., Bull. Acad. Sci. USSR, Div. Chem. Sci., 1976, vol. 25, no. 3, p. 517. https://doi.org/10.1007/BF01106644

    Article  Google Scholar 

  15. Bondarenko, N.A., Rudomino, M.V., and Tsvetkov, E.N., Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990, vol. 39, no. 5, p. 1076. https://doi.org/10.1007/BF00961729

    Article  Google Scholar 

  16. Tsvetkov, E.N., Bondarenko, N.A., Malakhova, I.G., and Kabachnik, M.I., Synthesis, 1986, vol. 1986, no. 3, p. 198. https://doi.org/10.1055/s-1986-31510

    Article  Google Scholar 

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ACKNOWLEDGMENTS

This study was supported by the Ministry of Science and Higher Education of the Russian Federation using the facilities of the joint center at the Kurchatov Institute and Center for Molecular Composition Studies at the Nesmeyanov Institute of Organoelement Compounds (Russian Academy of Sciences).

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Correspondence to N. A. Bondarenko.

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Bondarenko, N.A., Belus’, S.K., Artyushin, O.I. et al. New Tridentate Carbamoylmethylphosphine Oxides: Synthesis and NMR Spectra. Russ J Gen Chem 90, 2273–2280 (2020). https://doi.org/10.1134/S1070363220120099

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