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Organozinc reagents from polyfluoroarenes: Preparation and reactions with allyl halides. Synthesis of allylpolyfluoroarenes

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Abstract

Organozinc compounds of the general formula ArFZnX (X = Cl, ArF) were synthesized by reactions of Zn with chloropolyfluoroarenes and of Zn/SnCl2 with polyfluoroarenes. Polyflorinated organozinc compounds reacted with allyl chloride and allyl bromide to give the corresponding allyl-substituted polyfluoroarenes. The reactions with allyl chloride were carried out in the presence of copper(I) salts (CuCl or CuI).

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References

  1. White, W.L. and Filler, R., J. Chem. Soc. C, 1971, p. 2062.

  2. Haas, A. and Koehler, J., J. Fluorine Chem., 1981, vol. 17, p. 531.

    Article  CAS  Google Scholar 

  3. Rieke, R.D. and Rhyne, L.D., J. Org. Chem., 1979, vol. 44, p. 3445.

    Article  CAS  Google Scholar 

  4. Jukes, A.E., Dua, S.S., and Gilman, H., J. Organomet. Chem., 1970, vol. 24, p. 791.

    Article  CAS  Google Scholar 

  5. Burton, D.J., Yang, Z.-Y., and Morken, P.A., Tetrahedron, 1994, vol. 50, p. 2993.

    Article  CAS  Google Scholar 

  6. Albeniz, A.C., Espinet, P., and Martin-Ruiz, B., Chem. Eur. J., 2001, vol. 7, p. 2481.

    Article  CAS  Google Scholar 

  7. Harper, R.J., Jr., Soloski, E.J., and Tamborski, C., J. Org. Chem., 1964, vol. 29, p. 2385.

    Article  CAS  Google Scholar 

  8. Milner, D.J., J. Organomet. Chem., 1986, vol. 302, p. 147.

    Article  CAS  Google Scholar 

  9. Miller, A.O., Krasnov, V.I., Peters, D., Platonov, V.E., and Miethchen, R., Tetrahedron Lett., 2000, vol. 41, p. 3817.

    Article  CAS  Google Scholar 

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

    CAS  Google Scholar 

  11. Shteingarts, V.D., Kobrina, L.S., Bil’kis, I.I., and Starichenko, V.F., Khimiya poliftorarenov: mekhanizm reaktsii, intermediaty (Chemistry of Polyfluoroarenes: Reaction Mechanisms and Intermediates), Novosibirsk: Nauka, 1991, p. 272.

    Google Scholar 

  12. Kebarle, P. and Chowdhury, S., Chem. Rev., 1987, vol. 87, p. 513.

    Article  CAS  Google Scholar 

  13. Steelhammer, J.C. and Wehtworth, W.E., J. Chem. Phys., 1968, vol. 51, p. 1802.

    Article  Google Scholar 

  14. Vasil’eva, N.V., Starichenko, V.F., and Shchegoleva, L.N., Russ. J. Org. Chem., 1998, vol. 34, p. 1578.

    Google Scholar 

  15. Nguyen, Ba V. and Burton, D.J., J. Fluorine Chem., 1994, vol. 67, p. 205.

    Article  CAS  Google Scholar 

  16. Bordwell, F.G., Sokol, P.E., and Spainhour, J.D., J. Am. Chem. Soc., 1960, vol. 82, p. 2881.

    Article  CAS  Google Scholar 

  17. The Chemistry of Alkenes, Patai, S., Ed., London: Interscience, 1964.

    Google Scholar 

  18. Lange, H. and Naumann, D., J. Fluorine Chem., 1984, vol. 26, p. 435.

    Article  CAS  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 

  20. Tamborski, C. and Soloski, E.J., J. Org. Chem., 1966, vol. 31, p. 746.

    Article  CAS  Google Scholar 

  21. Chambers, R.D., Hall, C.W., Hutchinson, J., and Millar, R.W., J. Chem. Soc., Perkin Trans. 1, 1998, no. 10, p. 1705.

  22. Furin, G.G., Malyuta, N.G., Platonov, V.E., and Yakobson, G.G., Zh. Org. Khim., 1974, vol. 10, p. 830.

    CAS  Google Scholar 

  23. Evans, D.F. and Phillips, R.F., J. Chem. Soc., Dalton Trans., 1973, p. 978.

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Correspondence to V. E. Platonov.

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Dedicated to Full Member of the Russian Academy of Sciences G.A. Tolstikov on his 75th anniversary

Original Russian Text © A.S. Vinogradov, V.I. Krasnov, V.E. Platonov, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 1, pp. 101–107.

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Vinogradov, A.S., Krasnov, V.I. & Platonov, V.E. Organozinc reagents from polyfluoroarenes: Preparation and reactions with allyl halides. Synthesis of allylpolyfluoroarenes. Russ J Org Chem 44, 95–102 (2008). https://doi.org/10.1134/S1070428008010119

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  • DOI: https://doi.org/10.1134/S1070428008010119

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