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Russian Chemical Bulletin

, Volume 54, Issue 5, pp 1197–1202 | Cite as

Electrochemical N-arylation of azoles in MeOH using undivided electrolysis of their mixtures with 1,4-dimethoxybenzene

  • V. A. Petrosyan
  • A. V. Burasov
  • T. S. Vakhotina
Article

Abstract

The reactions of 1,4-dimethoxybenzene with azoles (pyrazole, triazole, and their derivatives, as well as tetrazole) were studied by undivided amperostatic electrolysis at Pt electrodes in MeOH. The process proceeds via the formation of a 1,1,4-trimethoxyarenonium cation as the key intermediate and affords 1,1,4,4-tetramethoxycyclohexa-2,5-diene, 1,1,4-trimethoxy-4-(azol-1-yl)cyclohexa-2,5-diene, and 1,4-dimethoxy-2-(azol-1-yl)benzene as the main products. Azole and solvent molecules compete as nucleophiles during electrolysis. A fine mechanism of the process was considered.

Key words

azoles 1,4-dimethoxybenzene paired electrosynthesis N-dimethoxyphenylazoles 

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Copyright information

© Springer Science+Business Media, Inc. 2005

Authors and Affiliations

  • V. A. Petrosyan
    • 1
  • A. V. Burasov
    • 1
  • T. S. Vakhotina
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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