Skip to main content
Log in

Stereoselective reduction of gem-dichlorocyclopropyl ethers

  • Organic Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    We have studied the partial and complete LiAlH4 reduction of gem-dichlorocyclopropyl ethers to 2-chlorocyclopropyl and cyclopropyl ethers.

  2. 2.

    In the partial reduction of gem-dichlorocyclopropyl ethers the chlorine atom cis to the substituent is selectivity reduced.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

Literature cited

  1. S. M. Shostakovskii, L. N. Aksenova, V. I. Erofeev, and V. S. Aksenov, Proceedings of the Fourth All-Union Conference on Acetylene Chemistry [in Russian], Vol. 2, Izd. Akad. Nauk KazakhSSR, Alma-Ata (1972), p. 354.

    Google Scholar 

  2. S. M. Shostakovskii and A. V. Bobrov, Zh. Org. Khim.,5, 908 (1969).

    Google Scholar 

  3. L. Sydnes and L. Skattebol, Tetrahedron Lett., 3703 (1974).

  4. C. W. Jefford, D. Kirkpatrick, and F. Delay, J. Am. Chem. Soc.,94, 8905 (1972).

    Google Scholar 

  5. J. Hatem and B. Waegell, Tetrahedron Lett., 2023 (1973).

  6. J. D. Morrison and H. S. Mosher, Asymmetric Organic Reactions, Prentice-Hall (1971).

  7. I. P. Beletskaya (editor), Ions and Ion Pairs in Organic Reactions [in Russian], Mir (1975), p. 156.

  8. M. Schlosser and G. Heinz, Angew Chem.,80, 849 (1968).

    Google Scholar 

  9. V. S. Aksenov and G. A. Terent'ev, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, No. 14, 114 (1974).

    Google Scholar 

  10. R. C. De Selms and T.-W. Lin, Tetrahedron,23, 1479 (1967).

    Google Scholar 

  11. A. A. Retinskii, Dissertation, Irkutsk (1974).

  12. G. Feugeas and I. P. Calv, Comptes Rendus Acad. Sci.,C266, No. 15, 1175 (1968).

    Google Scholar 

  13. S. M. Shostakovskii, L. I. L'vov, and Ya. M. Kimel'fel'd, Izv. Akad. Nauk SSSR, Ser. Khim., 1754 (1966).

  14. A. A. Retinskii, S. M. Shostakovskii, and É. I. Kositsyna, Izv. Akad. Nauk SSSR, Ser. Khim., 1778 (1972).

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 125–131, January, 1977.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shostakovskii, S.M., Voropaeva, T.K., Nikol'skii, N.S. et al. Stereoselective reduction of gem-dichlorocyclopropyl ethers. Russ Chem Bull 26, 107–112 (1977). https://doi.org/10.1007/BF00921504

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00921504

Keywords

Navigation