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Dimephosphone analogs: II. Dialkyl(diaryl)-(2-methyl-4-oxopent-2-yl)phosphine oxide oximes: Synthesis, structure, and generation of iminoxyl radicals

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Abstract

Dialkyl(diaryl)-(2-methyl-4-oxopent-2-yl)phosphine oxide oximes have been synthesized for the first time. According to the X-ray diffraction data, these compounds in crystal exist as a single E isomer. Their structure in solution and the E/Z isomer ratio were determined by 1H and 13C NMR spectroscopy.

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References

  1. Buzykin, B.I., Nabiullin, V.N., Mironova, E.V., Kostin, A.A., Tatarinov, D.A., Mironov, V.F., and Litvinov, I.A., Russ. J. Gen. Chem., 2012, vol. 82, no. 10, p. 1629.

    Article  CAS  Google Scholar 

  2. Vizel’, A.O. and Garaev, R.S., Novyi aspekt farmakologicheskogo podkhoda k soedineniyam fosfora. Dimefosfon (A new Aspect of Pharmacological Approach to Phosphorus Compounds. Dimephosphone), Kazan’, Pechat’-servis-XXI-vek, 2011.

    Google Scholar 

  3. Malyshev, V.G. and Fedoskin, I.V., Primenenie dimefosfona v meditsine (farmakoliticheskie, patogeneticheskie i klinicheskie aspekty) (Medical Application of Dimephosphone. Pharmacological, Pathogenetic, and Chemical Aspects), Moscow, Nauka, 2008.

    Google Scholar 

  4. Garaev, R.S., Zalyalyutdinova, L.N., Ovchinnikova, A.G., Kashapov, L.R., Vizel’, A.O., and Shchukina, L.I., Materialy nauchno-prakticheskoi konferentsii posvyashchennoi pamyati professora Ya.V. Kostina “Obshchestvo, zdorov’e, lekarstvo” (Proc. Scientific-Practical Conf. Dedicated to the Memory of Prof. Ya.V. Kostin “Socium, Health, Medicine), Saransk, 2005, p. 37.

    Google Scholar 

  5. Buzykin, B.I., Nabiullin, V.N., Mironov, V.F., Chestnova, R.V., Garaev, R.S., Kashapov, L.R., Mironova, E.V., Tatarinov, D.A., and Kostin, A.A., RF Patent no. 2 471 787, 2012; Byull. Izobret., 2012, no. 21.

    Google Scholar 

  6. Buzykin, B.I., Nabiullin, V.N., Mironov, V.F., Chestnova, R.V., Garaev, R.S., Kashapov, L.R., Mironova, E.V., Tatarinov, D.A., and Kostin, A.A., RF Patent no. 2 471 787, 2013; Byull. Izobret., 2013, no. 1.

    Google Scholar 

  7. Buzykin, B.I., Nabiullin, V.N., Garaev, R.S., Chestnova, R.V., Kashapov, L.R., Valiev, R.Sh., and Mironov, V.F., Pharm Chem. J., 2013, vol. 46, no. 1, p. 35.

    Article  Google Scholar 

  8. Mironov, V.F., Tatarinov, D.A., Baronova, T.A., Konovalov, A.I., Kostin, A.A., and Kryshtob, V.I., RF Patent no, 2 374 260, 2009; Byull. Izobret., 2009, no. 23.

    Google Scholar 

  9. Tatarinov, D.A., Mironov, V.F., Kostin, A.A., Baronova, T.A., and Buzykin, B.I., Russ. J. Gen. Chem., 2010, vol. 80, no. 7, p. 1377.

    Article  CAS  Google Scholar 

  10. Tatarinov, D.A., Mironov, V.F., Baronova, T.A., Kostin, A.A., Krivolapov, D.B., Buzykin, B.I., and Litvinov, I.A., Mendeleev Commun., 2010, vol. 20, no. 2, p. 86.

    Article  CAS  Google Scholar 

  11. Tatarinov, D.A., Kostin, A.A., Baronova, T.A., Dobrynin, A.B., Mironova, E.V., Krivolapov, D.B., Buzykin, B.I., and Mironov, V.F., Russ. J. Org. Chem., 2013, vol. 49, no. 4, p. 516.

    Article  CAS  Google Scholar 

  12. Nurtdinov, S.Kh., Khairullin, R.S., Tsivunin, V.S., Zykova, T.V., and Kamai, G.Kh., Zh. Obshch. Khim., 1970, vol. 40, no. 11, p. 2377.

    CAS  Google Scholar 

  13. Novitskii, K.I., Razumov, N.A., and Petrov, A.A., Khimiya organicheskikh soedinenii fosfora (Chemistry of Organic Phosphorus Compounds), Leningrad: Nauka, 1967, p. 248.

    Google Scholar 

  14. Arbuzov, B.A., Bel’skii, V.E., Vizel’, A.O., Ivanovskaya, K.M., and Motygullin, G.Z., Dokl. Akad. Nauk SSSR, 1967, vol. 176, no. 2, p. 323.

    CAS  Google Scholar 

  15. Nurtdinov, S.Kh., Tsivunin, V.S., Zykova, T.V., and Kamai, G.Kh., Zh. Obshch. Khim., 1967, vol. 37, no. 37, p. 692.

    CAS  Google Scholar 

  16. Elistratova, Yu.G., Mustafina, A.R., Tatarinov, D.A., Mironov, V.F., Burilov, V.A., Tananaev, I.G., and Konovalov, A.I., Russ. Chem. Bull., 2011, no. 5, p. 790.

    Google Scholar 

  17. Safiulina, A.M., Matveeva, A.G., Dvoryanchikova, T.K., Sinegribova, O.A., Tu, A.M., Tatarinov, D.A., Kostin, A.A., Mironov, V.F., and Tananaev, I.G., Russ. Chem. Bull., 2012, no. 2, p. 392.

    Google Scholar 

  18. Becker, C., Worek, F., and John, H., Drug Test. Anal., 2010, vol. 2, no. 10, p. 460.

    Article  CAS  Google Scholar 

  19. Delfino, R.T., Ribeiro, T.S., and Figueroa-Villar, J.D., J. Braz. Chem. Soc., 2009, vol. 20, no. 3, p. 407.

    Article  CAS  Google Scholar 

  20. Martynov, I.V., Sokolov, V.B., and Ivanov, A.N., Itogi Nauki Tekh., Ser. Org. Khim., 1989, vol. 10, p. 143.

    Google Scholar 

  21. Vizel’, A.O., Shchukina, L.I., Sharapova, S.M., Litvinov, I.A., and Gubaidullin, A.T., Ross. Khim. Zh., 1999, vol. 43, nos. 3–4, p. 152.

    Google Scholar 

  22. Shagidullin, R.R., Vandyukova, I.I., Zvereva, E.E., Vizel’, A.O., Shchukina, L.I., and Garaev, R.S., Russ. Chem. Bull., 2007, no. 7, p. 1298.

    Google Scholar 

  23. Afonin, A.V., Ushakov, I.A., Tarasova, O.A, Shmidt, E.Yu., Mikhaleva, A.I., and Voronov, V.K., Russ. J. Org. Chem., 2000, vol. 36, no. 12, p. 1777.

    CAS  Google Scholar 

  24. Afonin, A.V., Pavlov, D.V., Ushakov, I.A., Levanova, E.P., and Levkovskaya, G.G., Russ. J. Org. Chem., 2012, vol. 48, no. 3, p. 354.

    Article  CAS  Google Scholar 

  25. Il’yasov, A.V., Morozova, I.D., Vafina, A.A., and Zuev, M.B., Spektry EPR i stereokhimiya fosforsoderzhashchikh svobodnykh radikalov (ESR Spectra and Stereochemistry of Phosphorus-Containing Free Radicals), Moscow: Nauka, 1985.

    Google Scholar 

  26. Berski, S., Jaszewski, A.R., and Jezierska, J., Chem. Phys. Lett., 2001, vol. 341, no. 3, p. 168.

    Article  CAS  Google Scholar 

  27. Morozov, V.I., Buzykin, B.I., and Il’yasov, A.V., Russ. Chem. Bull., 2005, no. 2, p. 342.

    Google Scholar 

  28. Brokenshire, J.L., Roberts, J.R., and Ingold, K.U., J. Am. Chem. Soc., 1972, vol. 94, no. 20, p. 7040.

    Article  CAS  Google Scholar 

  29. Mendenhall, G.D. and Ingold, K.U., J. Am. Chem. Soc., 1973, vol. 95, no. 9, p. 2963.

    Article  CAS  Google Scholar 

  30. Eisenhauer, B.M., Wang, M., Brown, R.E., Labaziewicz, H., Ngo, M., Kettinger, K.W., and Mendenhall, G.D., J. Phys. Chem., 1997, vol. 10, no. 10, p. 737.

    CAS  Google Scholar 

  31. Sheldrick, G.M., SADABS, Madison, WI, USA: Bruker AXS, 1997.

    Google Scholar 

  32. Altomare, A., Cascarano, G., Giacovazzo, C., and Viterbo, D., Acta Crystallogr., Sect. A, 1991, vol. 47, no. 6, p. 744.

    Article  Google Scholar 

  33. Sheldrick, G.M., SHELX-97. Programs for Crystal Structure Analysis, Release 97-2. Göttingen, Germany, Univ. of. Göttingen, 1997, vols. 1, 2.

    Google Scholar 

  34. Farrugia, L.J., J. Appl. Crystallogr., 1999, vol. 32, p. 837.

    Article  CAS  Google Scholar 

  35. APEX2 (Version 2.1), SAINTPlus. Data Reduction and Correction Program (Version 7.31A). Bruker Advansed X-ray Solutions, Madison, WI, USA: Bruker AXS, 2006.

  36. Spek, A.L., Acta Crystallogr., Sect. A, 1990, vol. 46, no. 1, p. 34.

    Google Scholar 

  37. Farrugia, L.J., J. Appl. Crystallogr., 1997, vol. 30, p. 565.

    Article  CAS  Google Scholar 

  38. Cann, P.F., Howells, D., and Warren, S., J. Chem. Soc., Perkin Trans. 2, 1972, no. 3, p. 304.

    Google Scholar 

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Correspondence to D. A. Tatarinov.

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Original Russian Text © D.A. Tatarinov, V.F. Mironov, A.A. Kostin, E.V. Mironova, D.B. Krivolapov, V.I. Morozov, V.N. Nabiullin, A.V. Il’yasov, B.I. Buzykin, 2014, published in Zhurnal Obshchei Khimii, 2014, Vol. 84, No. 5, pp. 808–817.

For communication I, see [1].

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Tatarinov, D.A., Mironov, V.F., Kostin, A.A. et al. Dimephosphone analogs: II. Dialkyl(diaryl)-(2-methyl-4-oxopent-2-yl)phosphine oxide oximes: Synthesis, structure, and generation of iminoxyl radicals. Russ J Gen Chem 84, 901–910 (2014). https://doi.org/10.1134/S107036321405020X

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