Skip to main content
SpringerLink
Log in

Reaction of acetyloxiranes with acetonitrile

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

2-Acetyloxiranes react with acetonitrile in the presence of equimolar amounts of Lewis acids. It was established that the use of boron trifluoride etherate or sulfuric acid as the catalyst leads to 2,7- and 3,6-diepoxy-1,5-dioxocanes, the use of aluminum trichloride, as well as stannic chloride, leads to the corresponding chlorohydrins, while the use of gaseous boron trifluoride leads to 2-oxazolines in satisfactory yields. It is shown that the reaction is regio- and stereospecific and that the resulting substituted 2-methyl-5-acetyl-2-oxazolines have a cis configuration.

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. R. Oda, M. Okano, S. Tokiura, and F. Misuni, Bull. Chem. Soc. Jpn., 35, 1219 (1962).

    Google Scholar 

  2. T. I. Temnikova and T. E. Zhesko, Zh. Obshch. Khim., 33, 3436 (1963).

    Google Scholar 

  3. I. G. Tishchenko, O. N. Bubel', G. Z. Stasevich, and A. F. Abramov, Khim. Geterotsikl. Soedin., No. 7, 907 (1975).

    Google Scholar 

  4. F. Lazarini, Cryst. Struct. Commun., No. 5, 489 (1976).

    Google Scholar 

  5. V. M. Potapov, Stereochemistry [in Russian], Khimiya, Moscow (1976), p, 549.

    Google Scholar 

  6. S. O'Connor, W. I. O'Sullivan, E. M. Philbin, and C. P. Lillya, Chem. Ind., 12, 1225 (1966).

    Google Scholar 

  7. R. A. Wohl and J. Cannie, J. Org. Chem., 38, 1787 (1973).

    Google Scholar 

  8. 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 

  9. C. L. van Antwerp, J. Chem. Educ., 50, 639 (1973).

    Google Scholar 

  10. I. G. Tishchenko, in: Liquid-Phase Oxidation of Unsaturated Organic Compounds [in Russian], Minsk (1961), p. 73.

  11. I. N. Nazarov and A. A. Akhrem, Zh. Obshch. Khim., 80, 2189 (1950).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. V. I. Lenin Belorussian State University, 220080, Minsk

    O. N. Bubel', I. G. Tishchenko & Yu. L. Ptashnikov

  2. A. N. Sevchenko Scientific-Research Institute of Applied Physical Problems, 220106, Minsk

    O. N. Bubel', I. G. Tishchenko & Yu. L. Ptashnikov

Authors
  1. O. N. Bubel'
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. G. Tishchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yu. L. Ptashnikov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No, 8, pp. 1022–1024, August, 1982.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Bubel', O.N., Tishchenko, I.G. & Ptashnikov, Y.L. Reaction of acetyloxiranes with acetonitrile. Chem Heterocycl Compd 18, 773–775 (1982). https://doi.org/10.1007/BF00506574

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00506574

Keywords

Search

Navigation