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Electrophilic substitution at the aromatic carbon atom Communication 1. Cleavage of the C-Hg bond in the molecule of aromatic organomercury compounds under the action of halogens

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Summary

  1. 1.

    The kinetics of the electrophilic bimolecular reaction of phenylmercury bromide with bromine in the presence of ammonium bromide and with iodine in the presence of cadmium iodide were studied in a number of polar solvents.

  2. 2.

    In their influence on the reaction rate, the solvents are arranged in the following series; CH3OH>80% aqueous dioxane>DMF, obtained earlier for other organomercury compounds.

  3. 3.

    In all the solvents we studied the temperature dependence of the rates of the two reactions. The parameters of the Arrhenius equation were found.

  4. 4.

    The kinetics of the photochemical reaction of phenylmercury bromide with bromine and iodine in benzene was studied. The reaction possesses a summary first order.

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Literature cited

  1. 1.

    I. P. Beletskaya, O. A Reutov, and T. P. Gur'yanova, Izv. AN SSSR, Otd. Khim. N.,1961, 1589.

  2. 2.

    I. P. Beletskaya, O. A. Reutov, and T. P. Gur'yanova, Izv. AN SSSR, Otd. Khim. N.,1961, 1997.

  3. 3.

    I. P. Beletskaya, O. A. Reutov, and T. A. Azizyan, Izv. AN SSSR, Otd. Khim. N.,1962, 424.

  4. 4.

    I. P. Beletskaya, O. A. Reutov, and V. I. Karpov, Izv. AN SSSR, Otd. Khim. N.,1961, 1961.

  5. 5.

    I. P. Beletskaya, O. A. Reutov, and V. I. Karpov, Izv. AN SSSR, Otd. Khim. N.,1961, 2125.

  6. 6.

    I. P. Beletskaya, O. A. Reutov, and V. I. Karpov, Izv. AN SSSR, Otd. Khim. N.,1961, 2199.

  7. 7.

    A. Weisberger et al., Organic Solvents [Russian translation], IL, (1958), pp. 283, 302, 345, 436.

  8. 8.

    I. P. Beletskaya, O. A Reutov, and T. P. Gur'yanova, Izv. AN SSSR, Otd. Khim. N.,1961, 2178.

  9. 9.

    I P. Beletskaya, T. A. Azizyan, and O. A. Reutov, Izv. AN SSSR, Otd. Khim. N.,1962, 223.

  10. 10.

    I. P. Beletskaya, O. A. Reutov, and V. I. Karpov, Izv. AN SSSR, Ser. Khim.,1964, 1707.

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskay, No. 2, pp. 231–239, February, 1965

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Beletskaya, I.P., Érmanson, A.V. & Reutov, O.A. Electrophilic substitution at the aromatic carbon atom Communication 1. Cleavage of the C-Hg bond in the molecule of aromatic organomercury compounds under the action of halogens. Russ Chem Bull 14, 218–225 (1965). https://doi.org/10.1007/BF00845582

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Keywords

  • Cadmium
  • Iodine
  • Iodide
  • CH3OH
  • Dioxane