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Reaction of Phosphorus Trihalides with Methyl Triflate. Molecular and Supramolecular Structure of Methyltrichloro- and Methyltribromophosphonium Triflates

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Abstract

Prolonged (~4 years) keeping of mixtures of phosphorus trichloride or tribromide with methyl triflate in dark at 20–25°C has led to the formation of crystalline methyltrichloro- and methyltribromophosphonium triflates with a content of 10–11% in the reaction mixture and yield of 5–6%. Structure of the triflates has been elucidated by means of X-ray diffraction analysis.

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REFERENCES

  1. Clay, J.P., J. Org. Chem., 1951, vol. 16, no. 6, p. 892. https://doi.org/10.1021/jo01146a010

    Article  CAS  Google Scholar 

  2. Kinner, A.M. and Perren, E.A., J. Chem. Soc., 1952, p. 3437. https://doi.org/10.1039/JR9520003437

  3. Freedman, L.D. and Doak, G.O., Chem. Rev., 1957, vol. 57, no. 3, p. 479. https://doi.org/10.1021/cr50015a003

    Article  CAS  Google Scholar 

  4. Engel, R., Chem. Rev., 1977, vol. 77, no. 3, p. 349. https://doi.org/10.1021/cr60307a003

    Article  CAS  Google Scholar 

  5. Drug Discovery, El-Shemy, H.A., Ed., London: InTech, 2013, ch. 12, p. 325. https://doi.org/10.5772/52504

  6. Fields, S.C., Tetrahedron, 1999, vol. 55, no. 42, p. 12237. https://doi.org/10.1016/S0040-4020(99)00701-2

    Article  CAS  Google Scholar 

  7. Demmer, C.S., Krogsgaard-Larsen, N., and Bunch, L., Chem. Rev., 2011, vol. 111, no. 12, p. 7981. https://doi.org/10.1021/cr2002646

    Article  CAS  PubMed  Google Scholar 

  8. Zinov’ev, Yu.M. and Soborovskii, L.Z., Reaktsii i metody issledovaniya organicheskikh soedinenii (Reactions and Research Methods for Organic Compounds), Moscow: Khimiya, 1970, vol. 21, p. 6.

  9. du Mont, W.-W., Stenzel, V., Jeske, J., Jones, P.G., Sebald, A., Pohl, S., Saak, W., and Batcher, M., Inorg. Chem., 1994, vol. 33, no. 7, p. 1502. https://doi.org/10.1021/ic00085a047

    Article  CAS  Google Scholar 

  10. Politzer, P. and Murray, J.S., ChemPhysChem., 2013, vol. 14, no. 2, p. 278. https://doi.org/10.1002/cphc.201200799

    Article  CAS  PubMed  Google Scholar 

  11. Politzer, P., Murray, J.S., and Clark, T., PhysChemChemPhys., 2013, vol. 14, no. 27, p. 11178. https://doi.org/10.1039/C3CP00054K

    Article  Google Scholar 

  12. Lommerse, J.P.M., Stone, A.J., Taylor, R., and Allen, F.H., J. Am. Chem. Soc., 1996, vol. 118, no. 13, p. 3108. https://doi.org/10.1021/ja953281x

    Article  CAS  Google Scholar 

  13. Grabowski, S.J., Theor. Chem. Acc., 2013, vol. 132, no. 4, article no. 1347. https://doi.org/10.1007/s00214-013-1347-7

  14. Navon, O., Bernstein, J., and Khodorkovsky, V., Angew. Chem. Int. Ed., 1997, vol. 36, no. 6, p. 601. https://doi.org/10.1002/anie.199706011

    Article  CAS  Google Scholar 

  15. Straver, L.H. and Schierbeek, A.J., MOLEN. Structure Determination System. Program Description, Nonius B.V., 1994, vol. 1.

  16. Sheldrick, G.M., SHELX-97, Programs for Crystal Structure Analysis (Release 97-2). University of Gottingen, Germany, 1997.

  17. Farrugia, L.J., J. Appl. Cryst., 1999, vol. 32, no. 4, p. 837. https://doi.org/10.1107/S0021889899006020

    Article  CAS  Google Scholar 

  18. Spek, A.L., J. Appl. Cryst., 2003, vol. 36, no. 1, p. 7. https://doi.org/10.1107/S0021889802022112

    Article  CAS  Google Scholar 

  19. Macrae, C.F., Edgington, P.R., McCabe, P., Pidcock, E., Shields, G.P., Taylor, R., Towler, M., and van de Streek, J., J. Appl. Crystallogr., 2006. 39, no. 3, p. 453. https://doi.org/10.1107/S002188980600731X

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. A.E. Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”, 420088, Kazan, Russia

    A. T. Gubaidullin, V. F. Mironov & I. A. Litvinov

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  1. A. T. Gubaidullin
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  2. V. F. Mironov
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  3. I. A. Litvinov
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Correspondence to V. F. Mironov.

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Gubaidullin, A.T., Mironov, V.F. & Litvinov, I.A. Reaction of Phosphorus Trihalides with Methyl Triflate. Molecular and Supramolecular Structure of Methyltrichloro- and Methyltribromophosphonium Triflates. Russ J Gen Chem 90, 1630–1635 (2020). https://doi.org/10.1134/S1070363220090078

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