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Ene reaction of 4-phenyl-3H-1,2,4-triazole-3,5(4H)-dione with dicyclopentadiene

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Abstract

The kinetics of the ene reaction of endo-dicyclopentadiene with 4-phenyl-3H-1,2,4-triazole-3,5(4H)-dione in benzene, toluene, acetonitrile, 1,2-dichloroetane, and chloroform have been studied. The reaction volumes and enthalpies have been determined, and the activation volume in toluene has been calculated from the pressure kinetic data. The “anomalous” ratio ΔV ≠corr /ΔV r = 1.34 corresponds to a concerted cyclic transition state, though the addition product has acyclic structure.

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Authors and Affiliations

  1. Butlerov Institute of Chemistry, Kazan Federal University, ul. Kremlevskaya 18, Kazan, 420008, Tatarstan, Russia

    V. D. Kiselev, D. A. Kornilov, I. I. Lekomtseva & O. Yu. Reshetnikova

  2. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, ul. Arbuzova 8, Kazan, 420088, Tatarstan, Russia

    A. I. Konovalov

Authors
  1. V. D. Kiselev
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  2. D. A. Kornilov
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  3. I. I. Lekomtseva
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  4. O. Yu. Reshetnikova
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  5. A. I. Konovalov
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Correspondence to V. D. Kiselev.

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Dedicated to Full Member of the Russian Academy of Sciences V.I. Minkin on his 80th anniversary

Original Russian Text © V.D. Kiselev, D.A. Kornilov, I.I. Lekomtseva, O.Yu. Reshetnikova, A.I. Konovalov, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 3, pp. 397–400.

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Kiselev, V.D., Kornilov, D.A., Lekomtseva, I.I. et al. Ene reaction of 4-phenyl-3H-1,2,4-triazole-3,5(4H)-dione with dicyclopentadiene. Russ J Org Chem 51, 382–386 (2015). https://doi.org/10.1134/S1070428015030161

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  • DOI: https://doi.org/10.1134/S1070428015030161

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