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Reactions of Polyfluorinated 3-Substituted 2,4-Cyclohexadienones with Alkynes

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Abstract

Reactions of 2,3,4,5,6-pentafluoro-6-chloro-2,4-cyclohexadienone with anthranylic acid, 2,6-dichloro- and 2,6-dimethylaniline, diethylamine, sodium azide, and also the reaction of 6-phenyl-3-pentafluorophenoxy-2,4,5,6-tetrafluoro-2,4-cyclohexadienone with methanol afford 3-substituted 2,4,5,6-tetrafluoro-2,4-cyclohexadienones. The 3-methoxy-2,4,5,6-tetrafluoro-6-chloro-2,4-cyclohexadienone and 3-methoxy-6-phenyl-2,4,5,6-tetrafluoro-2,4-cyclohexadienone form cycloadducts with 1-hexyne and propargyl alcohol that under treatment with propyl alcohol in the presence of potassium carbonate undergo ring cleavage to furnish propyl arylfluorochloroacetates and diarylacetates. The reaction between 3-azido-2,4,5,6-tetrafluoro-6-chloro-2,4-cyclohexadienone and phenylacetylene gives rise to 4-oxo-2-phenyl-3,5,6,7-tetrafluoro-5-chlorobicyclo[4.1.0]hept-2-ene-7-carbonitrile.

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REFERENCES

  1. Mashkovskii, M.D., Lekarstvennye sredstva (Drugs), Kharkov: Torsing, 1998, vol. 1, 560p; vol. 2, 592 p.

    Google Scholar 

  2. Fluorine-Containing Molecules. Structure, Reactivity, Synthesis and Applications Liebman, J.F., Greenberg, A., and Dolbier, W.R., Eds., New York: VCH Publish. Inc., 1988.

    Google Scholar 

  3. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications Filler, R., Kobayashi, Y., and Yagupolskii, L.M., Eds., Amsterdam: Elsevier, 1983.

    Google Scholar 

  4. Biomedical Frontiers of Fluorine Chemistry Ojima, I., McCarthy, J.R., and Welch, J.T., ACS Symposium Series 639, Washington: DC, 1996.

  5. Kobrina, L.S. and Bogachev, A.A., J. Fluor. Chem. 1993, vol. 62, nos. 2-3, pp. 243-258.

    Google Scholar 

  6. Bogachev, A.A., Kobrina, L.S. and Shteingarts, V.D., Izv. Akad. Nauk, Ser. Khim. 1994, no. 9, pp. 1634-1637.

  7. Bogachev, A.A., Kobrina, L.S., Meyer, O.G.J., and Haufe, G., J. Fluor. Chem. 1999, vol. 97, nos. 1-2, pp. 135-143.

    Google Scholar 

  8. Akhmetova, N.E., Kostina, N.G., Mamatyuk, V.I., Shtark, A.A., and Shteingarts, V.D., Izv. SO Akad. Nauk SSSR, Ser. Khim. Nauk 1973, vol. 14, no. 6, pp. 86-100.

    Google Scholar 

  9. Battiste, M.A. and Posey, R.G., J. Fluor. Chem. 2000, vol. 102, no. 1-2, pp. 285-292.

    Google Scholar 

  10. Bogachev, A.A., Bagryanskaya, I.Yu., Rybalova, T.V., Gatilov, Yu.V., and Kobrina, L.S., Zh. Org. Khim. 1996, vol. 66, no. 8, pp. 1324-1333.

    Google Scholar 

  11. Kalinowski, H.-O., Berger, S., and Braun, S., 13 C NMR Spektroskopie Stuttgart-New York: Georg Thieme Verlag, 1984, p. 227.

    Google Scholar 

  12. Oehlschlager, A.C. and Zalkow, L.H., Chem. Commun. 1965, no. 4, pp. 70-71.

  13. Hedayatullah, M., Guy, A., and Hugneny, J.C., J. Heterocyclic Chem. 1984, vol. 21, no. 5, pp. 1385-1387.

    Google Scholar 

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  1. Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, Novosibirsk, 630090, Russia

    V. N. Kovtonyuk & L. S. Kobrina

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  1. V. N. Kovtonyuk
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  2. L. S. Kobrina
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Kovtonyuk, V.N., Kobrina, L.S. Reactions of Polyfluorinated 3-Substituted 2,4-Cyclohexadienones with Alkynes. Russian Journal of Organic Chemistry 38, 176–181 (2002). https://doi.org/10.1023/A:1015597112943

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