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Reactions of 1,2,4-trichlorotrifluorobenzene with nucleophiles

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Abstract

1,2,4-Trichlorotrifluorobenzene reacted with potassium hydrogen sulfide, potassium hydroxide, sodium isopropoxide, liquid ammonia, and ethyl cyanoacetate via nucleophilic substitution of one fluorine atom with predominant formation of the isomer in which the new substituent replaced fluorine atom in the 5-position.

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References

  1. Syntheses of Fluoroorganic Compounds, Knunyants, I.L. and Yakobson, G.G., Eds., Berlin Springer, 1985.

  2. Vorozhtsov, N.N., Platonov, V.E., and Yakobson, G.G., Bull. Acad. Sci. USSR, Div. Chem. Sci., 1963, vol. 12, no. 8, p. 1389.

    Article  Google Scholar 

  3. Yakobson, G.G., Platonov, V.E., and Vorozhtsov, N.N., Zh. Obshch. Khim., 1965, vol. 35, p. 1158.

    CAS  Google Scholar 

  4. Parshall, G.W., J. Org. Chem., 1962, vol. 27, p. 4649.

    Article  CAS  Google Scholar 

  5. Nikul’shin, P.V., Maksimov, A.M., and Platonov, V.E., Russ J. Org. Chem., 2012, vol. 48, p. 536.

    Article  Google Scholar 

  6. Sokolenko, V.I., L’vova, A.Ya., Tyurin, V.S., Platonov, V.E., and Yakobson, G.G., Zh. Org. Khim., 1970, vol. 6, p. 2496.

    CAS  Google Scholar 

  7. Krasnov, V.I. and Platonov, V.E., Russ. J. Org. Chem., 2000, vol. 36, p. 1488.

    CAS  Google Scholar 

  8. Allen, S.E., Mahatthananchai, J., Bode, J.W., and Kozlowski, M.C., J. Am. Chem. Soc., 2012, vol. 134, p. 12098.

    Article  CAS  Google Scholar 

  9. Chapyshev, S.V. and Chernyak, A.V., J. Fluorine Chem., 2013, vol. 156, p. 303.

    Article  CAS  Google Scholar 

  10. Budnik, A.G., Shteingarts, V.D., and Yakobson, G.G., Zh. Org. Khim., 1970, vol. 6, p. 1198.

    CAS  Google Scholar 

  11. Casares, J.A., Espinet, P., Martín-Alvarez, J.M., Martínez- Ilarduya, J.M., and Salas, G., Eur. J. Inorg. Chem., 2005, vol. 19, p. 3825.

    Article  Google Scholar 

  12. Ishikawa, N. and Hayashi, S., Nippon Kagaku Zasshi, 1968, vol. 89, p. 1131.

    Article  CAS  Google Scholar 

  13. Espinet, P., Martínez-Ilarduya, J.M., Peres-Briso, C., and Arturo, L.A.M., J. Organomet. Chem., 1998, vol. 551, p. 9.

    Article  CAS  Google Scholar 

  14. Shipilov, A.I., Karyukalova, N.N., and Igumnov, S.M., Russ. J. Org. Chem., 2002, vol. 38, p. 220.

    Article  CAS  Google Scholar 

  15. Mel’nikov, N.N., Khimiya i tekhnologiya pestitsidov (Chemistry and Technology of Pesticides), Moscow Khimiya, 1974.

    Google Scholar 

  16. Mel’nikov, N.N., Novozhilov, K.V., and Belan, S.R., Pestitsidy i regulyatory rosta rastenii. Spravochnik (Pesticides and Plant Growth Regulators. Reference Book), Moscow Khimiya, 1995.

    Google Scholar 

  17. Vaganova, T.A., Kusov, S.Z., Rodionov, V.I., Shundrina, I.K., and Malykhin, E.V., Russ. Chem. Bull., Int. Ed., 2007, vol. 56, p. 2239.

    Article  CAS  Google Scholar 

  18. Chambers, R.D., Close, D., and Williams, D.L.H., J. Chem. Soc., Perkin Trans. 2, 1980, p. 778.

    Google Scholar 

  19. Pushkina, L.N., Stepanov, A.P., Zhukov, V.S., and Naumov, A.D., Zh. Org. Khim., 1972, vol. 8, p. 586.

    CAS  Google Scholar 

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Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090, Russia

    P. V. Nikul’shin, A. M. Maksimov & V. E. Platonov

Authors
  1. P. V. Nikul’shin
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  2. A. M. Maksimov
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  3. V. E. Platonov
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Correspondence to P. V. Nikul’shin.

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Original Russian Text © P.V. Nikul’shin, A.M. Maksimov, V.E. Platonov, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 1, pp. 33–39.

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Nikul’shin, P.V., Maksimov, A.M. & Platonov, V.E. Reactions of 1,2,4-trichlorotrifluorobenzene with nucleophiles. Russ J Org Chem 52, 25–31 (2016). https://doi.org/10.1134/S107042801601005X

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  • DOI: https://doi.org/10.1134/S107042801601005X

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