Dependence of the decomposition rate of furoxanes on the polarity of the solvent

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Resumo

The decomposition rates of diphenylfuroxane and a number of 4-nitro-3-alkyl-furoxanes in dilute solutions were measured by manometric and calorimetric methods. In no case, an increase in the reaction rate was detected with an increase in the polarity of the solvent, which corresponds to the absence of an increase in the dipole moment of the molecule during the formation of a transition state. Based on this result, a conclusion is made about the biradical mechanism of decomposition of uncondensed disubstituted furoxanes in solutions.

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Sobre autores

G. Nazin

Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences

Email: akazakov@icp.ac.ru
Rússia, Chernogolovka

A. Kazakov

Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences

Autor responsável pela correspondência
Email: akazakov@icp.ac.ru
Rússia, Chernogolovka

A. Nabatova

Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences

Email: akazakov@icp.ac.ru
Rússia, Chernogolovka

L. Fershtat

Zelinsky Institute of Organic Chemistry, the Russian Academy of Sciences

Email: akazakov@icp.ac.ru
Rússia, Moscow

A. Larin

Zelinsky Institute of Organic Chemistry, the Russian Academy of Sciences

Email: akazakov@icp.ac.ru
Rússia, Moscow

Bibliografia

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  5. A. A. Larin, L. L. Fershtat, I. V. Ananyev, N. N. Makhova, Tetrahedron Lett. 58, 3993 (2017). https://doi.org/10.1016/j.tetlet.2017.09.013
  6. N. N. Makhova, L. L. Fershtat, Tetrahedron Lett. 59, 2317 (2018). https://doi.org/10.1016/j.tetlet.2018.04.070
  7. A. A. Larin, L. L. Fershtat, N. N. Makhova, Chem. Heterocycl. Compd. 56, 607 (2020). https://doi.org/10.1007/s10593-020-02706-4
  8. V. G. Prokudin, G. M. Nazin, G. B Manelis, Dokl. AN SSSR. 255, 917 (1980) [in Russian].
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  10. S. G. Entelis, R. P. Tiger, Kinetics of reactions in the liquid phase (Khimiya, Moscow, 1973) [in Russian].
  11. L. L. Fershtat, M. I. Struchkova, A. S. Goloveshkin, I. S. Bushmarinov, N. N. Makhova, Heteroat. Chem. 25, 226 (2014). https://doi.org/10.1002/hc.21166
  12. G. M. Nazin, V. V. Dubikhin, I. L. Dalinger, A. I. Kazakov, and A. V. Nabatova, Russ. J. Phys. Chem. B 15, 74 (2021). https://doi.org/10.1134/S1990793121010115
  13. G. M. Nazin, V. V. Dubikhin, T. K. Goncharov, A. I. Kazakov, A.V. Nabatova, and A.V. Shastin, Russ. J. Phys. Chem. B 15, 483 (2021). https://doi.org/10.1134/S1990793121030283
  14. L.N. Galperin, Yu.R. Kolesov, L.B. Mashkinov, Yu.E. Turner, Proc. Sixth All-Union Conf. on Calorimetry (Metsniereba, Tbilisi, 1973), p. 539 [in Russian].

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2. Molecular formula

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3. Fig. 1. Kinetic curves of the decomposition reaction of compound 1 at 234.6 °C in NB (1) and DF (2), and at 200 °C in NB (3) and DF (4).

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4. Fig. 2. Kinetic curves of decomposition of compounds 2g in DF (1) and NB (4), 2a in DF (2), in the melt (3) and in NB (5) at 200 °C.

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