Skip to main content
SpringerLink
Log in

Nucleophilic Addition to Acetylenes in Superbasic Catalytic Systems: X. Catalytic Effect of Alkali Metal Hydroxides in the Vinylation of 1-Heptanol

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

The catalytic activity of alkali metal hydroxides in base-catalyzed addition of 1-heptanol to acetylene depends on the alkali metal nature and degree of hydration of its hydroxide. In a closed system, the catalytic activity of alkali metal hydroxides decreases in the series 2KOH·H2O > RbOH·H2O > CsOH·H2O > NaOH. The corresponding series for a flow system is as follows: RbOH·H2O > CsOH·H2O > 2KOH·H2O > NaON > KOH·H2O. The difference is explained by participation of the catalyst in side reactions with both 1-heptanol and acetylene. Addition of dimethyl sulfoxide to the catalytic system accelerates the vinylation process.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

REFERENCES

  1. Parshina, L.N., Sokolyanskaya, L.V., Nosyreva, V.V., Scotheim, T., Zefirov, N.S., and Trofimov, B.A., Russ. J. Org. Chem., 1999, vol. 35, no. 2, pp. 202-206.

    Google Scholar 

  2. Akademik Aleksei Evgrafovich Favorskii. Izbrannye trudy (Academician Aleksei Evgrafovich Favorskii. Selected Papers), Moscow: Akad. Nauk SSSR, 1961.

  3. Shostakovskii, M.F., Prostye vinilovye efiry (Vinyl Ethers), Moscow: Akad. Nauk SSSR, 1952.

    Google Scholar 

  4. Reppe, W., Justus Liebigs Ann. Chem., 1956, vol. 601, pp. 81-138.

    Google Scholar 

  5. Kopenhaver, J. and Bigelou, M., The Chemistry of Acetylene and Related Compounds, Bergmann, E.D., Ed., New York: Intersci., 1948. Translated under the title Khimiya atsetilena, Moscow: Inostrannaya Literatura, 1954, pp. 174-239.

    Google Scholar 

  6. Shostakovskii, M.F., Trofimov, B.A., Atavin, A.S., and Lavrov, V.I., Usp. Khim., 1968, vol. 37, pp. 2070-2093.

    Google Scholar 

  7. Trofimov, B.A., Geteroatomnye proizvodnye atsetilena. Novye polifunktsional'nye monomery, reagenty i poluprodukty (Heteroatomic Acetylene Derivatives. New Polyfunctional Monomers, Reagents, and Intermediate Products), Moscow: Nauka, 1981.

    Google Scholar 

  8. Tedeschi, R.J., Encyclopedia of Physical Science and Technology, New York: Academic, 1992, vol. 1, pp. 27-65.

    Google Scholar 

  9. Miller, S.A., Acetylene, Its Properties, Manufacture, and Uses, London: Benn, 1966, vol. 2, pp. 198-245.

    Google Scholar 

  10. Miller, S.I. and Shkapenko, G., J. Am. Chem. Soc., 1955, vol. 77, no. 19, pp. 5038-5041.

    Google Scholar 

  11. Nagasawa, F. and Matsuzawa, K., J. Chem. Soc. Jpn., Ind. Chem. Sec., 1958, vol. 61, no. 1, pp. 28-33.

    Google Scholar 

  12. Otsuka, S., Matsui, Y., and Murahashi, S., Nippon Kagaku Zasshi, 1956, vol. 77, no. 5, pp. 766-773.

    Google Scholar 

  13. Otsuka, S., Matsui, Y., and Murahashi, S., Nippon Kagaku Zasshi, 1959, vol. 80, no. 10, pp. 1157-1160.

    Google Scholar 

  14. US Patent no. 1 866 328, 1932; Chem. Abstr., 1932, vol. 26, no. 16, p. 4345.

  15. US Patent no. 1 866 329, 1932; Chem. Abstr., 1932, vol. 26, no. 16, p. 4345.

  16. US Patent no. 1 866 430, 1932; Chem. Abstr., 1932, vol. 26, no. 16, p. 4345.

  17. Steinborn, D., Mosinski, H., and Rosenstock, T., J. Organomet. Chem., 1991, vol. 414, pp. 45-50.

    Google Scholar 

  18. Widon, B., Technique of Organic Chemistry, Weissberger, A., Ed., New York: Intersci., 1965, 3rd ed., vol. 11, part 2. Translated under the title Metody organicheskoi khimii. Ustanovlenie struktury organicheskikh soedinenii fizicheskimi i khimicheskimi metodami, Moscow: Khimiya, 1967, vol. XI, part II, pp. 234-290.

    Google Scholar 

  19. Trofimov, B.A., Usp. Khim., 1981, vol. 50, pp. 248-272.

    Google Scholar 

  20. Trofimov, B.A., Z. Chem., 1986, vol. 26, no. 2, pp. 41-49.

    Google Scholar 

  21. Trofimov, B.A., Zh. Org. Khim., 1986, vol. 22, no. 9, pp. 1991-2006.

    Google Scholar 

  22. Trofimov, B.A., Russ. J. Org. Chem., 1995, vol. 31, no. 9, pp. 1233-1252.

    Google Scholar 

  23. Steinborn, D., Rosenstock, T., and Sieler, J., J. Prakt. Chem., 1996, vol. 338, no. 3, pp. 264-269.

    Google Scholar 

  24. Trofimov, B.A., Oparina, L.A., Lavrov, V.I., and Parshina, L.N., Russ. J. Org. Chem., 1995, vol. 31, no. 5, pp. 597-600.

    Google Scholar 

  25. Miller, S.A., Acetylene, Its Properties, Manufacture, and Uses, London: Benn, 1966, vol. 1. Translated under the title Atsetilen, ego svoistva, poluchenie i primenenie, Leningrad: Khimiya, 1969, vol. 1, pp. 308-310.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Siberian Division, Russian Academy of Sciences, Favorskii Irkutsk Institute of Chemistry, ul. Favorskogo 1, Irkutsk, 664033, Russia

    L. N. Parshina, L. A. Oparina, O. V. Gorelova & B. A. Trofimov

  2. Ammonia Laboratory, BASF Actiengesellschaft, Ludwigshafen, Germany

    T. Preiss & J. Henkelmann

Authors
  1. L. N. Parshina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. A. Oparina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. O. V. Gorelova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. T. Preiss
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. J. Henkelmann
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. B. A. Trofimov
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Parshina, L.N., Oparina, L.A., Gorelova, O.V. et al. Nucleophilic Addition to Acetylenes in Superbasic Catalytic Systems: X. Catalytic Effect of Alkali Metal Hydroxides in the Vinylation of 1-Heptanol. Russian Journal of Organic Chemistry 37, 940–945 (2001). https://doi.org/10.1023/A:1012462113437

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1012462113437

Keywords

Search

Navigation