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Chemistry of Heterocyclic Compounds

, Volume 23, Issue 8, pp 849–854 | Cite as

Protic acid-induced intramolecular reactions of 2-cyclopropylazobenzenes

  • A. N. Fedotov
  • I. N. Shishkina
  • T. G. Kutateladze
  • S. S. Mochalov
  • Yu. S. Shabarov
Article

Abstract

Treatment of 2-cyclopropylazobenzenes with concentrated sulfuric acid affords the intramolecular N- and C-alkylation products. Treatment of azobenzenes with trifluoroacetic acid results in quantitative rearrangement to arylindazoles via the intermediate formation of acid-stable indazolium ions. It is suggested that the formation of indazolium ions in trifluoroacetic acid results from the synchronous opening of the cyclopropane ring and stabilization of the developing carbocation by an internal nucleophile (the azo-group).

Keywords

Organic Chemistry Sulfuric Acid Cyclopropane Trifluoroacetic Acid Intermediate Formation 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1988

Authors and Affiliations

  • A. N. Fedotov
    • 1
  • I. N. Shishkina
    • 1
  • T. G. Kutateladze
    • 1
  • S. S. Mochalov
    • 1
  • Yu. S. Shabarov
    • 1
  1. 1.M. V. Lomonosov State UniversityMoscow

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