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

V. D. Filimonov, S. G. Gorbachev, E. E. Sirotkina

Research output: Contribution to journalArticle

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.

Original languageEnglish
Pages (from-to)252-255
Number of pages4
JournalChemistry of Heterocyclic Compounds
Volume16
Issue number3
DOIs
Publication statusPublished - 1 Mar 1980

ASJC Scopus subject areas

  • Organic Chemistry

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