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Fluorine-containing Heterocycles: XI. 5(6)-Fluoro-6(5)-X-benzofuroxans: Synthesis, Tautomerism, and Transformations

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Abstract

Features of 5(6)-fluoro-6(5)-X-benzofuroxans tautomerism were investigated. By 1H, 13C, and 19F NMR spectroscopy the direction of Boulton-Katritzky rearrangement in nitration, nitrosation, and azo coupling of fluorine-containing furoxanes was determined.

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REFERENCES

  1. Lipunova, G.N., Nosova, E.V., Kodess, M.I., and Charushin, V.N., Zh. Org. Khim., 2004, vol. 40, p. 1209.

    Google Scholar 

  2. Khmel'nitskii, L.I., Novikov, S.S., and Godovikova, T.I., Khimiya furoxanov (reaktsii i primenenie) (Chemistry of Furoxanes (Reactions and Application), Moscow: Nauka, 1996, p. 104.

    Google Scholar 

  3. Frutero, R., Ferratori, B., Serafino, A., Di, Stilo, A., and Gasco, A., J. Heterocyclic Chem., 1989, vol. 26, p. 1345.

    Google Scholar 

  4. Busigina, O.G., Pyatakova, N.V., Hropov, U.V., Ovchinnikov, N.I., Makhova, N.I., and Severina, I.S., Biochemistry, 2000, vol. 65, p. 540.

    Google Scholar 

  5. Okiyama, N., Uchiyama, S., Onoda, M., Imai, K., and Santa, T., Heterocycles, 2002, vol. 58, p. 165.

    Google Scholar 

  6. Liebman, J.F., Greenberg, A., and Dolbier, W.R., Fluorine-Containing Molecules. Structure Reactivity Synthesis and Applications, VCH Publishers. Inc., 1998, p. 346.

  7. Filler, R., Kobayashi, I., and Jagupolskii, L.M., Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications, Amsterdam: Elsevier Science, Publishers, 1993, p. 386.

    Google Scholar 

  8. Kotovskaya, S.K., Charushin, V.N., Chupakhin, O.N., and Kozhevnikova, E.O., Zh. Org. Khim., 1998, vol. 34, p. 399.

    Google Scholar 

  9. Kotovskaya, S.K., Perova, N.M., Charushin, V.N., and Chupakhin, O.N., Mendeleev Commun., 1999, p. 76.

  10. Chupakhin, O.N., Kotovskaya, S.K., Perova, N.M., Baskakova, Z.M., and Charushin, V.N., Khim. Geterotsikl. Soed., 1999, vol. 4, p. 520.

    Google Scholar 

  11. Kotovskaya, S.K., Romanova, S.A., Charushin, V.N., Kodess, M.I., and Chupakhin, O.N., J. Fluorine Chem., 2004, vol. 125, p. 421.

    Google Scholar 

  12. Boulton, A.J., Gripper, Gray, A.C., and Katrizky, A.R., J. Chem. Soc. (B), 1967, p. 909.

  13. Pople, J.A., Schneider, W.G., and Bernstein, H.J., High Resolution Nuclear Magnetic Resonance, New York: McGraw-Hill., 1959, p. 222.

    Google Scholar 

  14. Michinori, Oki,Application of Dynamic NMR Spectroscopy to Organic Chemistry, VCH Publishers. Inc., 1985, p. 423.

  15. Shanan-Atidi, Bar-Eli. J. Phys. Chem., 1970, vol. 74, p. 961.

    Google Scholar 

  16. Boulton, A.J., Ghosh, H.B., and Katrizky, A.R., J. Chem. Soc. (B), 1966, p. 1004.

  17. Boulton, A.J. and Katritzky, A.R., Rev. Chim. Acad. Rep. Pop'roum., 1962, p. 691.

  18. Allen, F.H., Kennard, O., Watson, D.G., Brammer, L., Orpin, A.G., and Taylor, R., J. Chem. Soc., Perkin Trans. II, 1987, p. 1.

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Authors and Affiliations

  1. Ural State Technical University, Yekaterinburg, 620219, Russia

    O. N. Chupakhin & S. K. Kotovskaya

  2. Postovskii Institute of Organic Synthesis, Ural Division, Russian Academy of Sciences, Yekaterinburg, 620219, Russia

    S. A. Romanova & V. N. Charushin

Authors
  1. O. N. Chupakhin
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  2. S. K. Kotovskaya
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  3. S. A. Romanova
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  4. V. N. Charushin
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Chupakhin, O.N., Kotovskaya, S.K., Romanova, S.A. et al. Fluorine-containing Heterocycles: XI. 5(6)-Fluoro-6(5)-X-benzofuroxans: Synthesis, Tautomerism, and Transformations. Russian Journal of Organic Chemistry 40, 1167–1174 (2004). https://doi.org/10.1023/B:RUJO.0000045900.28273.c3

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  • DOI: https://doi.org/10.1023/B:RUJO.0000045900.28273.c3

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