Chemistry of Heterocyclic Compounds

, Volume 16, Issue 3, pp 252–255 | Cite as

9-Alkenylcarbazoles. 6. Synthesis and structure of cis-9-propenylcarbazoles

  • V. D. Filimonov
  • S. G. Gorbachev
  • E. E. Sirotkina
Article
  • 39 Downloads

Abstract

A number of cis-9-propenylcarbazoles were synthesized in good yields by isomerization of 9-allylcarbazoles by the action of tert-BuOK in dimethyl sulfoxide. It was established that cis-9-propenylcarbazole is less thermodynamically stable than its trans isomer. It was shown by13C NMR, UV, and IR spectroscopy that the effect of p-π conjugation in cis-9-propenylcarbazole decreases as compared with the trans isomer as a result of the noncoplanarity of the C=C bond and the carbazole ring.

Keywords

Spectroscopy Organic Chemistry Dimethyl Sulfoxide Dimethyl Sulfoxide 

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Copyright information

© Plenum Publishing Corporation 1980

Authors and Affiliations

  • V. D. Filimonov
    • 1
  • S. G. Gorbachev
    • 1
  • E. E. Sirotkina
    • 1
  1. 1.S. M. Kirov Tomsk Polytechnic InstituteTomsk

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