ELECTROCHEMICAL OXIDATIVE AROMATIZATION OF 9-SUBSTITUTED 9,10-DIHYDROACRIDINES: CLEAVAGE OF C–H <i>vs</i> C–X BOND

Authors

  • Oleg N. Chupakhin Postovsky Institute of Organic Synthesis, Russian Academy of Sciences, 20 Akademicheskaya / 22 S. Kovalevskoi St., Yekaterinburg 620990 Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002
  • Alexandr V. Shchepochkin Postovsky Institute of Organic Synthesis, Russian Academy of Sciences, 20 Akademicheskaya / 22 S. Kovalevskoi St., Yekaterinburg 620990 Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002
  • Valery N. Charushin Postovsky Institute of Organic Synthesis, Russian Academy of Sciences, 20 Akademicheskaya / 22 S. Kovalevskoi St., Yekaterinburg 620990 Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002
  • Anna V. Maiorova Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002 Institute of Metallurgy, Ural Branch of the Russian Academy of Sciences, 101 Amundsena St., Yekaterinburg 620016
  • Tatyana V. Kulikova Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002 Institute of Metallurgy, Ural Branch of the Russian Academy of Sciences, 101 Amundsena St., Yekaterinburg 620016
  • Konstantin Yu. Shunyaev Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002 Institute of Metallurgy, Ural Branch of the Russian Academy of Sciences, 101 Amundsena St., Yekaterinburg 620016
  • Andrey N. Enyashin Institute of Solid State Chemistry, Ural Branch of the Russian Academy of Sciences, 91 Pervomaiskaya St., Yekaterinburg 620990
  • Pavel A. Slepukhin Postovsky Institute of Organic Synthesis, Russian Academy of Sciences, 20 Akademicheskaya / 22 S. Kovalevskoi St., Yekaterinburg 620990 Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002
  • Anna I. Suvorova Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002

DOI:

https://doi.org/10.1007/5098

Keywords:

acridines, dihydroacridines, bond dissociation energy, C–H functionalization, electrochemical oxidation, SNH reactions, thermodynamic studies

Abstract

Reactivity of dihydroacridines bearing a С–X fragment at the geminal C-9 atom (where X = C, N, O, P, S) on anode has been investigated by means of electrochemical oxidation and thermodynamic and quantum-chemical calculations. The electrochemical oxidation results either in the formation of the 9-substituted acridines or in the cleavage of the C–X bond. This dual behavior of dihydroazines is analogous to processes reported in literature that take place upon treatment with chemical oxidants.

Downloads

Published

2019-09-26

Issue

Vol. 55 No. 10 (2019)

Section

Original Papers