Skip to main content
SpringerLink
Log in

Electrochemical bromoalkoxylation of 2-alkoxy-δ5-dihydropyrans

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A number of 2,6-dialkoxy-3-bromotetrahydropyrans were obtained by the electrochemical bromomethoxylation of 2-alkoxy-Δ 5-dihydropyrans. An assumption regarding the stereo-specificity of the electrochemical and chemical bromoalkoxylation was stated on the basis of the dehydrobromination and hydrogenation of the compounds obtained and on the basis of the results of gas-liquid chromatography: the reaction proceeds as cis and trans addition at the multiple bond, and the alkoxy group occupies only the trans position with respect to the alkoxy group already present in the ring. The isomeric 2,6-dialkoxy-Δ 4-dihydropyrans are formed along with 2,6-dialkoxy-Δ 3-dihydropyrans in the dehydrobromination of 2,6-dialkoxy-3-bromotetrahydropyrans.

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. S. M. Makin, V. M. Likhosherstov, and M. I. Shelemina, Zh. Obshch. Khim., 34, 1809 (1964).

    Google Scholar 

  2. J. Korte, A. Bilow, and R. Heinz, Tetrahedron, 18, 657 (1962).

    Google Scholar 

  3. N. K. Kochetkov, L. I. Kudryashov, N. V. Molodtsov, and E. D. Khomutova, Zh. Obshch. Khim., 31, 3909 (1961).

    Google Scholar 

  4. O. A. Reutov, Theoretical Foundations of Organic Chemistry [in Russian], Izd. MGU, Moscow (1964), p. 231.

    Google Scholar 

  5. I. Saunders, Ionic Reactions in the Aliphatic Series [Russian translation], Mir, Moscow (1967), p. 32.

    Google Scholar 

  6. N. S. Zefirov, N. M. Shekhtman, and R. A. Karakhanov, Zh. Organ. Khim., 3, 1925 (1967).

    Google Scholar 

  7. R. H. Hall and B. K. Horve, J. Chem. Soc., 2480 (1951).

  8. A. Kankaanperä and K. Müki, Acta Chem. Scand., 23, 1471 (1969).

    Google Scholar 

  9. L. N. Kralinina, R. I. Kruglikova, and T. P. Tarulina, Khim. Geterotsikl. Soedin., 311 (1970).

  10. M. Cahu and G. Descotes, Bull. Soc. Chim. France, 2975 (1968).

Download references

Author information

Authors and Affiliations

  1. M. V. Lomonosov Moscow Institute of Precision Chemical Engineering, USSR

    R. I. Kruglikova & L. N. Kralinina

Authors
  1. R. I. Kruglikova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. N. Kralinina
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 875–878, July, 1972.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kruglikova, R.I., Kralinina, L.N. Electrochemical bromoalkoxylation of 2-alkoxy-δ5-dihydropyrans. Chem Heterocycl Compd 8, 792–795 (1972). https://doi.org/10.1007/BF00475203

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00475203

Keywords

Search

Navigation