Advertisement

Chemistry of Heterocyclic Compounds

, Volume 32, Issue 2, pp 153–157 | Cite as

Polyfuryl(aryl)alkanes and their derivatives. 12. C-fur bond cleavage in the series of polyfuryl(aryl)alkanes

  • A. V. Butin
  • T. A. Stroganova
  • V. G. Kul'nevich
Article
  • 41 Downloads

Abstract

Reactions taking place with cleavage of the C-Fur bond are examined. It was established that disproportionation in two directions, leading to the formation of tris(5-methyl-2 furyl)methane, takes place when 3, 4dimethoxyphenylbis(5-methyl-2 furyl)methane is boiled in an acidic medium. The acid-catalyzed reaction of 5-methylfurfural with ethylene glycol leads to the formation of either 2-(S-methyl-2 fury!)-1,3-dioxolane or tris(S-methyl-2 furyl)methane, depending on the catalyst. The treatment of 2-(S-methyl-2 fury!)-1,3-dioxolane or gem-tris(5. methyl-2 furyl)ethane with triryl perchlorate leads to tris(5-methyl-2 furyl)carbenium or bis(5-methyl-2-furyl)methylcarbenium perchlorates respectively.

Keywords

Ethylene Methane Organic Chemistry Ethylene Glycol Alkane 
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.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    T. A. Stroganova, A. V. Butin, V. T. Abaev, and V. E. Zavodnik, Khim. Geterotsikl. Soedin., No. 2, 168 (1996) [in this issue].Google Scholar
  2. 2.
    G. A. Olah, R. H. Schlosberg, R. D. Porter, Y. K. Mo, D. P. Kelli, and G. D. Mateescu, J. Am. Chem. Soc.,94, 2034 (1972).Google Scholar
  3. 3.
    V. F. Lavrushin, Dokl. Akad. Nauk SSSR, 45, 809 (1954).Google Scholar
  4. 4.
    A. P. Yakubov, D. V. Tsyganov, L. I. Belen'kii, and M. M. Krayushkin, Zh. Org. Khim.,26, 1976 (1990).Google Scholar
  5. 5.
    K. Bauer and R. Mölleken, German Patent No. 2,418,974; Ref. Zh. Khim., 11N172 (1977).Google Scholar
  6. 6.
    R. G. Mölleken and K. A. Bauer, Chem. Ztg.,104, 226 (1980).Google Scholar
  7. 7.
    A. F. Pozharskii, Theoretical Principles of the Chemistry of Heterocycles (in Russian], Khimiya, Moscow (1985).Google Scholar
  8. 8.
    E. B. Usova, G. D. Krapivin, and V. G. Kul'nevich, Khim. Geterotsikl. Soedin., No. 9, 1289 (1992).Google Scholar
  9. 9.
    E. B. Usova, G. D. Krapivin, L. 1. Lysenko, and V. G. Kul'nevich, Khim. Geterotsikl. Soedin., No. 11, 1289 (1993).Google Scholar
  10. 10.
    A. V. Butin, V. T. Abaev, V. E. Zavodnik, and V. G. Kul'nevich, Khim. Geterotsikl. Soedin., No. 5, 627 (1993).Google Scholar
  11. 11.
    A. V. Butin and V. G. Kul'nevich, Khim. Geterotsikl. Soedin., No. 4, 566 (1992).Google Scholar
  12. 12.
    A. V. Butin, V. G. Kul'nevich, V. T. Abaev, and O. Yu. Okhlobystin, Khim. Geterotsikl. Soedin., No. 8, 1141 (1992).Google Scholar
  13. 13.
    H. Meerwein, K. Bodenbenner, P. Borner, F. Kunert, and K. Wunderlich, Annalen,632, 38 (1960).Google Scholar
  14. 14.
    V. V. Mezheritskii, E. P. Olekhnovich, S. M. Luk'yanov, and G. N. Dorofeenko, Ortho Esters in Organic Synthesis [in Russian], Izd. Rostovsk. Un-ta, Rostov-on-Don (1976), p. 38.Google Scholar
  15. 15.
    P. S. Clezy, C. J. R. Fookes, D. Y. K. Lau, A. W. Nichol, and G. A. Smythe, Aust. J. Chem.,27, 357 (1974).Google Scholar
  16. 16.
    Z. I. Zelikman, L. A. Falina, A. I. Shkrebets, and V. G. Kul'nevich, Khim. Khim. Tekhnol.,16, No. 9, 54 (1973).Google Scholar
  17. 17.
    A. V. Butin, V. G. Kul'nevich, V. T. Abaev, N. G. Mikhailyuchenko, A. V. Shpakov, O. Yu. Okhlobystin, V. E. Zavodnik, and A. I. Lutsenko, Khim. Geterotsikl. Soedin., No. 3, 329 (1993).Google Scholar
  18. 18.
    V. G. Kul'nevich, L. A. Solonenko, and S. B. Zhuravlev, Khim. Geterotsikl. Soedin., No. 5, 592 (1983).Google Scholar

Copyright information

© Plenum Publishing Corporation 1996

Authors and Affiliations

  • A. V. Butin
    • 1
  • T. A. Stroganova
    • 1
  • V. G. Kul'nevich
    • 1
  1. 1.Kubansk State Technological UniversityKrasnodar

Personalised recommendations