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).
Similar content being viewed by others
References
White, W.L. and Filler, R., J. Chem. Soc. C, 1971, p. 2062.
Haas, A. and Koehler, J., J. Fluorine Chem., 1981, vol. 17, p. 531.
Rieke, R.D. and Rhyne, L.D., J. Org. Chem., 1979, vol. 44, p. 3445.
Jukes, A.E., Dua, S.S., and Gilman, H., J. Organomet. Chem., 1970, vol. 24, p. 791.
Burton, D.J., Yang, Z.-Y., and Morken, P.A., Tetrahedron, 1994, vol. 50, p. 2993.
Albeniz, A.C., Espinet, P., and Martin-Ruiz, B., Chem. Eur. J., 2001, vol. 7, p. 2481.
Harper, R.J., Jr., Soloski, E.J., and Tamborski, C., J. Org. Chem., 1964, vol. 29, p. 2385.
Milner, D.J., J. Organomet. Chem., 1986, vol. 302, p. 147.
Miller, A.O., Krasnov, V.I., Peters, D., Platonov, V.E., and Miethchen, R., Tetrahedron Lett., 2000, vol. 41, p. 3817.
Krasnov, V.I. and Platonov, V.E., Russ. J. Org. Chem., 2000, vol. 36, p. 1488.
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.
Kebarle, P. and Chowdhury, S., Chem. Rev., 1987, vol. 87, p. 513.
Steelhammer, J.C. and Wehtworth, W.E., J. Chem. Phys., 1968, vol. 51, p. 1802.
Vasil’eva, N.V., Starichenko, V.F., and Shchegoleva, L.N., Russ. J. Org. Chem., 1998, vol. 34, p. 1578.
Nguyen, Ba V. and Burton, D.J., J. Fluorine Chem., 1994, vol. 67, p. 205.
Bordwell, F.G., Sokol, P.E., and Spainhour, J.D., J. Am. Chem. Soc., 1960, vol. 82, p. 2881.
The Chemistry of Alkenes, Patai, S., Ed., London: Interscience, 1964.
Lange, H. and Naumann, D., J. Fluorine Chem., 1984, vol. 26, p. 435.
Pushkina, L.N., Stepanov, A.P., Zhukov, V.S., and Naumov, A.D., Zh. Org. Khim., 1972, vol. 8, p. 586.
Tamborski, C. and Soloski, E.J., J. Org. Chem., 1966, vol. 31, p. 746.
Chambers, R.D., Hall, C.W., Hutchinson, J., and Millar, R.W., J. Chem. Soc., Perkin Trans. 1, 1998, no. 10, p. 1705.
Furin, G.G., Malyuta, N.G., Platonov, V.E., and Yakobson, G.G., Zh. Org. Khim., 1974, vol. 10, p. 830.
Evans, D.F. and Phillips, R.F., J. Chem. Soc., Dalton Trans., 1973, p. 978.
Author information
Authors and Affiliations
Corresponding author
Additional information
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.
Rights and permissions
About this article
Cite this article
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
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428008010119