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Chemistry of Heterocyclic Compounds

, Volume 29, Issue 8, pp 883–888 | Cite as

Synthesis and electrophilic trichloromethylation of 2,4-dialkylthiophenes. Some transformations of 2,4-di-tert-butyl-5-(trichloromethyl)thiophene

  • L. I. Belen'kii
  • G. P. Gromova
  • M. M. Krayushkin
Article

Abstract

The disproportionation products of the C-protonation of 5-tert-butyl-2-methyl- and 2-ethylthiophene first give 4-tert-butyl-2-methyl- and 2-ethylthiophene. We studied the electrophilic trichloromethylation of a series of 2,4-dialkyl thiophenes and showed that the reaction goes smoothly only for the most sterically hindered 2,4-di-tertbutyl-thiophene. We studied the reaction of 2,4-di-tert-butyl-5-(trichloromethyl)thiophene with some O- and N-nucleophiles.

Keywords

Organic Chemistry Thiophene Disproportionation Trichloromethyl Disproportionation Product 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    L. I. Belen'kii, G. P. Gromova, and M. M. Krayushkin, Gazz. Chim. Ital., 120, 365 (1990).Google Scholar
  2. 2.
    M. M. Krayushkin, A. A. Loktionov, and L. I. Belen'kii, Khim. Geterotsikl. Soedin., No. 8, 1037 (1988).Google Scholar
  3. 3.
    L. I. Belen'kii and A. P. Yakubov, Tetrahedron, 40, 2471 (1984).Google Scholar
  4. 4.
    L. I. Belen'kii and A. P. Yakubov, Tetrahedron, 42, 759 (1986).Google Scholar
  5. 5.
    L. I. Belen'kii, Khim. Geterotsikl. Soedin., No. 6, 733 (1992).Google Scholar
  6. 6.
    L. I. Belen'kii, D. B. Brokhovetskii, and M. M. Krayushkin, Chem., Scripta, 29, 81 (1989).Google Scholar
  7. 7.
    L. I. Belen'kii, A. P. Yakubov, Yu. K. Sudarushkin, and Ya. L. Gol'dfarb, Zh. Org. Khim., 9, 1621 (1973).Google Scholar
  8. 8.
    D. B. Brokhovetskii, L. I. Belen'kii, and M. M. Krayushkin, Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1692 (1990).Google Scholar
  9. 9.
    D. B. Brokhovetskii, Synthesis and Reactions of Trichloromethylarenes with Heteronucleophiles. Cand. Chem. Sci. Dissertation, Moscow (1990).Google Scholar
  10. 10.
    D. B. Brokhovetskii, L. I. Belen'kii, and M. M. Krayushkin, Izv. Akad. Nauk SSSR, Ser. Khim., No. 3, 748 (1989).Google Scholar
  11. 11.
    L. I. Belen'kii, D. B. Brokhovetskii, and M. M. Krayushkin, Tetrahedron, 47, 447 (1991).Google Scholar
  12. 12.
    A. Hantzsch and A. Lucas, Chem. Ber., 28, 744 (1895).Google Scholar
  13. 13.
    E. C. Spaeth and C. B. Germain, J. Amer. Chem. Soc., 77, 4066 (1955).Google Scholar
  14. 14.
    Organic Syntheses [Russian translation], Coll. Vol. 2, Inostr. Lit., Moscow (1949), p. 76.Google Scholar
  15. 15.
    E. Campaigne and W. L. Archer, J. Amer. Chem. Soc., 75, 989 (1953).Google Scholar
  16. 16.
    R. Lantz and A.-B. Hornfeldt, Chem. Scripta, 2, 9 (1972).Google Scholar

Copyright information

© Plenum Publishing Corporation 1994

Authors and Affiliations

  • L. I. Belen'kii
    • 1
  • G. P. Gromova
    • 1
  • M. M. Krayushkin
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryRussian Academy of SciencesMoscow

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