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Effect of pressure on the bromination of ring-substituted toluenes by N-bromosuccinimide

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    Study has been made of the effect of pressures ranging up to 6000 kgf/cm2 on the bromination of ring-substituted toluenes by N-bromosuccinimide. Increase of pressure increases the rate of benzyl H atom detachment by Br atoms, the effect being most pronounced in systems in which the bromination rate at atmospheric pressure is low.

  2. 2.

    A linear correlation has been established (for the first time) between the substituent a constant and the difference in the activation volume effects (ΔV ≠R -ΔV ≠T ) in the substituted and unsubstituted toluenes. It is clear that this difference in volume effects does not arise from solvation processes.

  3. 3.

    The Hammett equation applies to the bromination of substituted toluenes by N-bromosuccinimide at all pressures, theρ value for any such reaction falling off sharply as the pressure rises.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    M. Ya. Botnikov, I. Kh. Milyavskaya & V. M. Zhulin

Authors
  1. M. Ya. Botnikov
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  2. I. Kh. Milyavskaya
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  3. V. M. Zhulin
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 577–581, March, 1977.

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Botnikov, M.Y., Milyavskaya, I.K. & Zhulin, V.M. Effect of pressure on the bromination of ring-substituted toluenes by N-bromosuccinimide. Russ Chem Bull 26, 517–521 (1977). https://doi.org/10.1007/BF01179457

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  • DOI: https://doi.org/10.1007/BF01179457

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