Skip to main content
SpringerLink
Log in

Synthesis of 2-substituted tetrahydrofurans

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

We have developed a three-stage scheme for the preparative synthesis of 2-substituted tetrahydrofurans from allyl halides and aldehydes to give the first stage — a Grignard reaction — mixed alkoxides, which on treatment with acetic anhydride are converted to 4-acetoxy-1-alkenes. Addition of hydrogen bromide to the latter contrary to Markownikoff's rule gives 4-acetoxy-1-bromoalkanes, which as a result of hydrolysis form 2-R-tetrahydrofurans.

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

Literature Cited

  1. Yu. K. Yur'ev and I. P. Gragerov, Zh. Obshch. Khim., 19, 724 (1949).

    Google Scholar 

  2. R. Onesta and A. Ferretti, Gazz. Chim. Ital., 85, 288 (1955).

    Google Scholar 

  3. I. F. Bel'skii and N. I. Shuikin, Dokl. Akad. Nauk SSSR, 128, 945 (1959).

    Google Scholar 

  4. I. F. Bel'skii and N. I. Shuikin, The Chemistry of Organosulfur Compounds Contained in Oils and Petroleum Products [in Russian], Vol. 4, GNTI Neftyanoi i Gorno-toplivnoi Lit., Moscow (1961), p. 17.

    Google Scholar 

  5. E. N. Karaulova, The Chemistry of Petroleum Sulfides [in Russian], Nauka, Moscow (1970), p. 61.

    Google Scholar 

  6. Organicum [Russian translation], Vol. 2, Mir, Moscow (1979), pp. 140, 141.

  7. J. Cousseau and M. Lamant, Bull. Soc. Chim. France, No. 12, 4702 (1967).

    Google Scholar 

  8. N. I. Shuikin and B. A. Lebedev, Izv. Akad. Nauk SSSR, Ser. Khim., No. 3, 639 (1967).

    Google Scholar 

  9. Yu. K. Yur'ev, V. I. Gusev, V. A. Tronova, and P. P. Yurilin, Zh. Obshch. Khim., 11, 344 (1941).

    Google Scholar 

  10. B. W. Renfrow, D. Oakes, C. Lauer, and T. A. Walter, J. Org. Chem., 26, 935 (1961).

    Google Scholar 

  11. K. Weigand and G. Hilgetag, Experimental Methods in Organic Chemistry [Russian translation], Khimiya, Moscow (1968), p. 117.

    Google Scholar 

  12. S. DoleŽal, Chem. Comm., 2638 (1965).

  13. N. P. Volynskii and L. I. Perepelitchenko, Neftekhimiya, 27, No. 2, 266 (1987).

    Google Scholar 

  14. J. Colonge and M. Reymermier, Compt. Rend., 237, 266 (1953).

    Google Scholar 

  15. R. Consden, D. Duveen, and J. Kenyon, J. Chem. Soc., 2106 (1938).

  16. G. Wagner, Berichte, 27, 2434 (1894).

    Google Scholar 

  17. N. A. Ryabinin, I. P. Kolenko, and B. N. Lundin, Tr. Inst. Khim. Ural'sk. Fil. Akad. Nauk SSSR, No. 16, 80 (1968).

    Google Scholar 

  18. N. A. Ryabinin and I. P. Kolenko, Khim. Geterotsikl. Soedin., No. 1, 8 (1968).

    Google Scholar 

  19. V. G. Bukharov and T. E. Pozdnyakova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 1, 135 (1961).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. A. V. Topchiev Institute of Petrochemical Synthesis, Academy of Sciences of the USSR, 117912, Moscow

    N. P. Volynskii & L. I. Perepelitchenko

Authors
  1. N. P. Volynskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. I. Perepelitchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1604–1607, December, 1988.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Volynskii, N.P., Perepelitchenko, L.I. Synthesis of 2-substituted tetrahydrofurans. Chem Heterocycl Compd 24, 1324–1327 (1988). https://doi.org/10.1007/BF00486670

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00486670

Keywords

Search

Navigation