9-Alkenylcarbazoles. 10. 13C NMR spectra of 9-vinyl- and cis- and trans-9-propenylcarbazoles

V. D. Filimonov, V. A. Anfinogenov, S. G. Gorbachev

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The 13C NMR spectra of a number of ring-substituted 9-vinylcarbazoles and cis- and trans-9-propenylcarbazoles were studied. It was found that the CB chemical shifts of the vinyl atoms of these compounds correlate satisfactorily with the σ constants of the substituents in the 3 and 6 position of the carbazolyl rings; the slopes of the straight lines increase in the order 5.84, 7.68, 9.56. The inductive and conjugation components of the effect of the substituents on the chemical shifts of the CB atoms were evaluated. It follows from the results obtained that the effects of p-π conjugation are realized not only in the relatively planar isomers but also in the nonplanar cis isomers of 9-alkenylcarbazoles.

Original languageEnglish
Pages (from-to)1265-1269
Number of pages5
JournalChemistry of Heterocyclic Compounds
Issue number12
Publication statusPublished - Dec 1982

ASJC Scopus subject areas

  • Organic Chemistry

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