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Variable Activity of Reagents with C=C and N=N Bonds in Cycloaddition Reactions

  • XXIX Russian Symposium “Modern Chemical Physics” (Tuapse, Russia, September 2017)
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Abstract

Data on rates and enthalpies of the reactions of quadricyclane (4) and diadamantylidene (5) with N-phenylmaleimide (1), 4-phenyl-1,2,4-triazoline-3,5-dione (2), and tetracyanoethylene (3) are obtained for the first time. Reagent 2 with the N=N reaction center is found to be six orders of magnitude more active than its structural analog 1. A strong π-acceptor 3 is 370 times more active than reagent 2 in the reaction with a strong π-donor substrate 4 but is less active than reagent 2 in many [4π + 2π], [2π + 2π + 2π], and [2π + 2π] cycloaddition reactions, and, especially, in ene reactions. The possible causes of the strong difference and variable activity of compounds 1–3 with C=C and N=N bonds are discussed.

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Authors and Affiliations

  1. Butlerov Institute of Chemistry, Kazan (Volga Region) Federal University, Kazan, Tatarstan, Russia

    O. V. Anikin, D. A. Kornilov, T. V. Nikitina & V. D. Kiselev

Authors
  1. O. V. Anikin
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  2. D. A. Kornilov
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  3. T. V. Nikitina
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  4. V. D. Kiselev
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Corresponding author

Correspondence to V. D. Kiselev.

Additional information

Original Russian Text © O.V. Anikin, D.A. Kornilov, T.V. Nikitina, V.D. Kiselev, 2018, published in Khimicheskaya Fizika, 2018, Vol. 37, No. 8, pp. 3–6.

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Anikin, O.V., Kornilov, D.A., Nikitina, T.V. et al. Variable Activity of Reagents with C=C and N=N Bonds in Cycloaddition Reactions. Russ. J. Phys. Chem. B 12, 595–598 (2018). https://doi.org/10.1134/S1990793118040176

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  • DOI: https://doi.org/10.1134/S1990793118040176

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