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Pyrroles from ketoximes and acetylene

V. Study of the transmission of substituent effects in 1-vinyl-2-arylpyrroles by 13C NMR spectroscopy

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Chemistry of Heterocyclic Compounds Aims and scope

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Abstract

On the basis of a comparative study and analysis of the chemical shifts in the 13C NMR spectra of 1-vinyl-2-arylpyrroles and 3-alkyl-1-vinyl-2-phenylpyrroles, as well as 2-phenyl- and 1-ethyl-2-phenylpyrroles, it was established that the effects of substituents in the investigated series are transmitted via a mechanism involving conjugation and π induction; the conductivity and polarizability of the 2-arylpyrrole system increase when a vinyl group is introduced in the 1 position or, in the case of the 1-vinylpyrrole system, when a phenyl group is introduced in the 2 position; this is due to the increase in the degree of overall conjugation.

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Authors and Affiliations

  1. Irkutsk Institute of Organic Chemistry, Siberian Branch of the Academy of Sciences of the USSR, 664033, Irkutsk

    B. A. Trofimov, M. V. Sigalov, V. M. Bzhezovskii, G. A. Kalabin, S. E. Korostova, A. I. Mikhaleva & L. N. Balabanova

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  1. B. A. Trofimov
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  2. M. V. Sigalov
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  3. V. M. Bzhezovskii
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  4. G. A. Kalabin
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  5. S. E. Korostova
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  6. A. I. Mikhaleva
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  7. L. N. Balabanova
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Additional information

See [1] for communication IV.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 768–772, June, 1978.

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Trofimov, B.A., Sigalov, M.V., Bzhezovskii, V.M. et al. Pyrroles from ketoximes and acetylene. Chem Heterocycl Compd 14, 626–630 (1978). https://doi.org/10.1007/BF00481135

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  • DOI: https://doi.org/10.1007/BF00481135

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