Chemistry of Heterocyclic Compounds

, Volume 11, Issue 2, pp 144–146 | Cite as

Synthesis of 2-alkoxy-Δ3-dihydropyrans from Δ2-dihydropyrans

  • V. B. Mochalin
  • A. N. Kornilov
Article
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Abstract

Some 2-alkoxy-Δ3-dihydropyrans can be easily obtained by bromoalkoxylation with N-bromosuccinimide in the presence of alcohols of various Δ2-dihydropyrans and subsequent dehydrobromination of the resulting alkoxybromides with alcoholic alkali. The stereospecificity of this transformation was studied in the case of 6-substituted Δ2-dihydropyrans.

Keywords

Alcohol Organic Chemistry Alcoholic Alkali 

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Literature cited

  1. 1.
    F. Korte, A. Bilow, and R. Heinz, Tetrahedron, 18, 657 (1962).Google Scholar
  2. 2.
    V. B. Mochalin, Z. I. Smolina, and B. V. Unkovskii, Zh. Organ. Khim., 5, 2224 (1969).Google Scholar
  3. 3.
    A. Banaszek and A. Zamojski, Roczn. Chem., 45, 859 (1971).Google Scholar
  4. 4.
    D. G. Kubler, J. Org. Chem., 27, 1435 (1962).Google Scholar
  5. 5.
    O. A. Shavrygina and S. M. Makin, Zh. Organ. Khim., 2, 1354 (1966).Google Scholar
  6. 6.
    G. F. Woods and H. Sanders, J. Amer. Chem. Soc., 68, 2483 (1946).Google Scholar
  7. 7.
    S. M. Makin, V. M. Likhosherstov, and M. I. Shelemina, Zh. Obshch. Khim., 34, 1809 (1964).Google Scholar
  8. 8.
    V. B. Mochalin, Yu. N. Porshnev, and G. I. Samokhvalov, Zh. Obshch. Khim., 39, 681 (1969).Google Scholar
  9. 9.
    V. B. Mochalin, Yu. N. Porshnev, and G. I. Samokhvalov, Zh. Obshch. Khim., 39, 701 (1969).Google Scholar
  10. 10.
    V. B. Mochalin, A. N. Kornilov, A. N. Vul'fson, and I. S. Varpakhovskaya, Khim. Geterotsikl. Soedin., 167 (1975).Google Scholar
  11. 11.
    R. J. Ferrier and G. H. Sankey, J. Chem. Soc., C, 2339, 2345 (1966).Google Scholar
  12. 12.
    S. D. Yablonovskaya, N. M. Shekhtman, N. D. Antonova, S. V. Bogatkov, S. M. Makin, and N. S. Zefirov, Zh. Organ. Khim., 6, 871 (1970).Google Scholar

Copyright information

© Plenum Publishing Corporation 1976

Authors and Affiliations

  • V. B. Mochalin
    • 1
  • A. N. Kornilov
    • 1
  1. 1.M. V. Lomonosov Moscow Institute of Fine Chemical TechnologyUSSR

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