Skip to main content
SpringerLink
Log in

Reactions of acyloxiranes with aliphatic ketones

Synthesis of 4-acyl-1,3-dioxolanes

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Acyloxiranes react with aliphatic ketones in the presence of boron trifluoride etherate to give the corresponding 4-acyl-1,3-dioxolanes. The corresponding 4,5s-dimethyl-4r-acetyl-1,3-dioxolanes are formed in this case from 2,3t-dimethyl-2r-acetyloxirane, whereas a mixture of cis- and trans-1,3-dioxolanes is formed from trans-2-acetyl-3-phenyloxirane and acetone. The reaction of acyloxiranes with unsymmetrical ketones gives a mixture of the cis- and trans-1,3-dioxolanes with respect to the substituents attached to C-2 relative to the acetyl group, whereas the isomer ratio in this case depends on the effective volumes of the substituents attached to C-2.

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. I. G. Tishchenko, O. N. Bubel', and G. Z. Stasevich, Khim. Geterotsikl. Soedin., 885 (1974).

  2. B. N. Blackett, J. M. Coxon, M. P. Hartshorn, A. J. Lewis, G. R. Little and G. J. Wright, Tetrahedron, 26, 1311 (1970).

    Google Scholar 

  3. P. Salomaa and A. KanKaaperä, Acta Chem. Scand., 15, 871 (1961).

    Google Scholar 

  4. S. A. Barker, E. J. Bourne, R. M. Pinkard, M. Stacey, and D. H. Whiffen, J. Chem. Soc., 3232 (1958).

  5. H. J. Lucas and M. S. Guthrie, J. Amer. Chem. Soc., 72, 5490 (1950).

    Google Scholar 

  6. J. S. Josan and F. W. Eastwood, Austr. J. Chem., 21, 2013 (1968).

    Google Scholar 

  7. W. E. Willy, G. Binsch, and E. L. Eliel, J. Amer. Chem. Soc., 92, 5394 (1970).

    Google Scholar 

  8. L. M. Jackman and S. Sternhell, Application of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, New York (1969), p. 288.

  9. M. J. Karplus, J. Amer. Chem. Soc., 85, 2870 (1963).

    Google Scholar 

  10. F. A. L. Anet and J. M. Muchowski, Chem. Ind., 81 (1963).

  11. L. H. Zalkow and M. Ghosal, Chem. Commun., 922 (1967).

  12. J. Chuche, G. Dana, and M.-R. Monot, Bull. Soc. Chim. France, 3300 (1967).

  13. E. Baer and H. O. L. Fisher, J. Biol. Chem., 128, 463 (1939).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. V. I. Lenin Belorussian State University, Minsk

    I. G. Tishchenko, O. N. Bubel', G. Z. Stasevich & A. F. Abramov

Authors
  1. I. G. Tishchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. O. N. Bubel'
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. Z. Stasevich
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. F. Abramov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 907–910, July, 1975.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Tishchenko, I.G., Bubel', O.N., Stasevich, G.Z. et al. Reactions of acyloxiranes with aliphatic ketones. Chem Heterocycl Compd 11, 795–798 (1975). https://doi.org/10.1007/BF00497296

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00497296

Keywords

Search

Navigation