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Formation of free radicals in the vinylation of 2-substituted pyrroles with acetylenes in a KOH-DMSO system

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

By spin trapping, using 2-methyl-2-nitrosopropane (t-BuNO), the EPR signals of vinyl-tert-butylnitroxyls and spin adducts of t-BuNO with products of the addition of 2-substituted pyrrole radicals to acetylenes were recorded during the vinylation of 2-substituted pyrroles with acetylenes in a KOH-DMSO system. The 2-substituted pyrrole radicals have a high stability, and their EPR spectra were observed directly in the vinylation reactions. It is shown that one-electron transfer processes are involved in vinylation.

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References

  1. B. A. Trofimov, T. I. Vakul'skaya, S. E. Korostova, S. G. Shevchenko, and A. I. Mikhaleva, Izv. Akad. Nauk, Ser. Khim., No. 1, 142 (1990).

    Google Scholar 

  2. V. N. Belevskii and S. P. Yarkov, Dokl. Akad. Nauk SSSR, 254, 1417 (1980).

    Google Scholar 

  3. I. M. Sosonkin, V. N. Belevskii, G. N. Strogov, A. N. Domarev, and S. P. Yarkov, Zh. Org. Khim., 18, 1504 (1982).

    Google Scholar 

  4. G. F. Dvorko and E. A. Shilov, Teor. Éksp. Khim., 3, 606 (1967).

    Google Scholar 

  5. R. W. Zoellner and K. J. Klabunde, Chem. Rev., 84, 545 (1984).

    Google Scholar 

  6. V. V. Pen'kovskii and Yu. A. Kruglyak, Zh. Strukt. Khim., 10, 459 (1969).

    Google Scholar 

  7. A. Bartl, G. Freudenberg, J. Frohner, B. Pietrac, and L. Wuckel, Makromol. Chem., 184, 2187 (1983).

    Google Scholar 

  8. A. L. Buchachenko and A. M. Vasserman, Stable Radicals [in Russian], Khimiya, Moscow (1973).

    Google Scholar 

  9. H. G. Aurich and F. Baer, Angew. Chem., 79, 1070 (1967).

    Google Scholar 

  10. W. Ahrens, K. Wieser, and A. Berndt, Tetrahedron, 31, 2829 (1975).

    Google Scholar 

  11. H. G. Aurich, G. Blinni, and W. Dersoh, Ann., 762, 154 (1972).

    Google Scholar 

  12. C. M. Camaggi, R. J. Holman, and M. J. Perkins, J. Chem. Soc., Perkin Trans. 2, No. 5, 501 (1972).

    Google Scholar 

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Authors and Affiliations

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

    T. I. Vakul'skaya, B. A. Trofimov, A. I. Mikhaleva, S. E. Korostova, S. G. Shevchenko & L. I. Sobenina

Authors
  1. T. I. Vakul'skaya
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  2. B. A. Trofimov
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  3. A. I. Mikhaleva
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  4. S. E. Korostova
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  5. S. G. Shevchenko
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  6. L. I. Sobenina
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Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1056–1062, August, 1992.

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Vakul'skaya, T.I., Trofimov, B.A., Mikhaleva, A.I. et al. Formation of free radicals in the vinylation of 2-substituted pyrroles with acetylenes in a KOH-DMSO system. Chem Heterocycl Compd 28, 884–889 (1992). https://doi.org/10.1007/BF00531319

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  • DOI: https://doi.org/10.1007/BF00531319

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