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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Authors and Affiliations

  1. S. M. Kirov Tomsk Polytechnic Institute, 634004, Tomsk

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

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  1. V. D. Filimonov
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  2. S. G. Gorbachev
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  3. E. E. Sirotkina
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Additional information

See [1] for communication 5.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 340–343, March, 1980.

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Filimonov, V.D., Gorbachev, S.G. & Sirotkina, E.E. 9-Alkenylcarbazoles. 6. Synthesis and structure of cis-9-propenylcarbazoles. Chem Heterocycl Compd 16, 252–255 (1980). https://doi.org/10.1007/PL00020565

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  • DOI: https://doi.org/10.1007/PL00020565

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