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Chemistry of Heterocyclic Compounds

, Volume 28, Issue 11, pp 1260–1263 | Cite as

Oxidation, bromination, and methylenation of carbazole and (E)-3-(2-phenylethenyl)carbazole with HBr/DMSO

  • M. S. Yusubov
  • E. A. Krasnokutskaya
  • V. D. Filimovov
  • L. F. Kovaleva
Article

Abstract

It is shown that oxidation of (E)-3-(2-phenylethenyl)-9-methylcarbazole with HBr/DMSO leads to the formation of 1-(6-bromo-9-methylcarbazol-3-yl)-2-phenylethane-1,2-dione. In the case of (E)-3-(2-phenylethenyl)carbazole, methylenation occurs with formation of 9,9′-bis[3-(2-phenylethane-1,2-dionyl)-6-bromocarbazolyl]methane in addition to oxidation of the double bond and bromination of the phenyl ring. This reagent can also be successfully used for the preparative bromination and methylenation of certain carbazoles.

Keywords

Oxidation Methane Organic Chemistry Phenyl Double Bond 
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 1993

Authors and Affiliations

  • M. S. Yusubov
    • 1
  • E. A. Krasnokutskaya
    • 1
  • V. D. Filimovov
    • 1
  • L. F. Kovaleva
    • 1
  1. 1.Tomsk Polytechnical UniversityTomsk

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