Skip to main content
SpringerLink
Log in

Acylation of Cyclopropyl-Substituted Alkenes with Complexes Formed by ω-(Ethylthio)alkanoyl Fluorides and Boron Trifluoride

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Cyclopropyl-substituted alkenes react with complexes formed by boron trifluoride and 3-(ethylthio)propionyl fluoride and 2-(ethylthio)acetyl fluoride to give ketones containing an ethylthio group. In most cases the reaction is not accompanied by opening of the three-membered ring or rearrangements.

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

REFERENCES

  1. Groves, J.K., Chem. Soc. Rev., 1972, vol. 1, no. 1, pp. 73-97.

    Google Scholar 

  2. Adams, D.R., Bratnagar, S.P., and Cookson, R.C., J. Chem. Soc., Perkin Trans. 1, 1975, no. 15, pp. 1502-1506.

  3. Shastin, A.V. and Balenkova, E.S., Zh. Org. Khim., 1983, vol. 19, no. 3, pp. 659-660.

    Google Scholar 

  4. Gridnev, I.D. and Balenkova, E.S., Zh. Org. Khim., 1990, vol. 26, no. 1, pp. 46-53.

    Google Scholar 

  5. Verteletskii, P.V. and Balenkova, E.S., Zh. Org. Khim., 1990, vol. 26, no. 11, pp. 2446-2447.

    Google Scholar 

  6. Nenaidenko, V.G., Verteletskii, P.V., and Balenkova, E.S., Vestn. Mosk. Gos. Univ., Ser. 2: Khim., 1996, vol. 37, no. 6, pp. 540-543.

    Google Scholar 

  7. Nenaidenko, V.G. and Balenkova, E.S., Zh. Org. Khim., 1992, vol. 28, no. 3, pp. 600-602.

    Google Scholar 

  8. Nenaidenko, V.G. and Balenkova, E.S., Zh. Org. Khim., 1993, vol. 29, no. 4, pp. 687-688.

    Google Scholar 

  9. Nenajdenko, V.G., Leshcheva, I.F., and Balenkova, E.S., Tetrahedron, 1994, vol. 50, no. 3, pp. 775-782.

    Google Scholar 

  10. Nenajdenko, V.G., Gridnev, I.D., and Balenkova, E.S., Tetrahedron, 1994, vol. 50, no. 37, pp. 11 023-11 038.

    Google Scholar 

  11. Nenajdenko, V.G. and Balenkova, E.S., Tetrahedron, 1994, vol. 50, no. 43, pp. 12 407-12 414.

    Google Scholar 

  12. Nenajdenko, V.G., Lebedev, M.V., and Balenkova, E.S., Tetrahedron Lett., 1995, vol. 36, no. 35, pp. 6317-6320.

    Google Scholar 

  13. Nenajdenko, V.G., Lebedev, M.V., and Balenkova, E.S., Synlett., 1995, no. 11, pp. 1133-1134.

  14. Salaun, The Chemistry of the Cyclopropyl Group, Rappoport, Z., Ed., Chichester: Wiley, 1987, p. 809.

    Google Scholar 

  15. Vasil'ev, A.A. and Balenkova, E.S., Zh. Org. Khim., 1983, vol. 19, no. 2, pp. 288-291.

    Google Scholar 

  16. Vasil'ev, A.A., Luzikov, Yu.N., and Balenkova, E.S., Zh. Org. Khim., 1984, vol. 20, no. 5, pp. 1007-1012.

    Google Scholar 

  17. Vasil'ev, A.A., Balenkova, E.S., Levashova, T.V., Grigor'ev, A.A., Smirnova, N.V., and Luzikov, Yu.N., Zh. Org. Khim., 1981, vol. 17, no. 9, pp. 2018-2019.

    Google Scholar 

  18. Mooradian, A., Cavallito, C.G., Bergman, A.J., Lawson, E.S., and Suter, S.M., J. Am. Chem. Soc., 1949, vol. 71, no. 10, pp. 3372-3374.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Faculty of Chemistry, Moscow State University, Vorob'evy gory, Moscow, 119899, Russia

    M. V. Lebedev, V. G. Nenaidenko, K. I. Smolko & E. S. Balenkova

Authors
  1. M. V. Lebedev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. G. Nenaidenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. K. I. Smolko
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. E. S. Balenkova
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Lebedev, M.V., Nenaidenko, V.G., Smolko, K.I. et al. Acylation of Cyclopropyl-Substituted Alkenes with Complexes Formed by ω-(Ethylthio)alkanoyl Fluorides and Boron Trifluoride. Russian Journal of Organic Chemistry 37, 326–333 (2001). https://doi.org/10.1023/A:1012390420551

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1012390420551

Keywords

Search

Navigation