Skip to main content
Log in

[3,3]-Sigmatropic rearrangements of the acetoacetates of allyl alcohols (Carroll reaction) and allylphenyl ethers (Claisen reaction) on the surface of adsorbents

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

Abstract

A method has been developed for effecting rearrangements of allylacetoacetates to γ,δ-unsaturated ketones (Carroll rearrangement) and allylaryl ethers to the corresponding allylphenols (Claisen rearrangement) under conditions of adsorption on aluminum oxide and silica gel. The method provides a sharp reduction of the temperature of these reactions and improvement of their efficiency.

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. O. Simonian, W. A. Smit, A. S. Gybin, et al., Tetrahedron Lett.,27, 1245 (1986).

    Google Scholar 

  2. V. A. Smit, S. O. Simonyan, V. A. Tarasov, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 12, 2796 (1988).

    Google Scholar 

  3. L. A. Yanovskaya, Reactions and Methods of Investigation of Organic Compounds [in Russian], Book 2, Gos. Nauchn.-Tekhn. Izd-vo Khim. Lit., Moscow (1963), pp. 259–308.

    Google Scholar 

  4. S. R. Wilson and M. F. Price, J. Org. Chem.,49, 722 (1981).

    Google Scholar 

  5. Organic Reaction, Vol. 22, Wiley, New York (1975), p. 1.

  6. R. P. Lutz, Chem. Rev.,84, No. 2, 206 (1984).

    Google Scholar 

  7. F. M. Sonnenberg, J. Org. Chem.,35, 3166 (1970).

    Google Scholar 

  8. J. Borgulya, R. Madeja, P. Fahrni, et al., Helv. Chim. Acta,56, 14 (1973).

    Google Scholar 

  9. I. N. Nazarov, B. P. Gusev, and V. I. Gunar, Zh. Obshch. Khim.,28, 1444 (1958).

    Google Scholar 

  10. C. Weygand and G. Hilgetag (eds.), Organisch-chemische ExperimentierKunst, 3rd ed., Barth, Leipzig (1964).

    Google Scholar 

  11. W. Kimel, N. N. Sax, S. Kaiser, et al., J. Org. Chem.,23, 153 (1958).

    Google Scholar 

  12. Organic Reactions [Russian translation], No. 2, IL, Moscow (1950), pp. 7–60.

  13. Gy. Frater and H. Schmid., Helv. Chim. Acta,50, 255 (1967).

    Google Scholar 

  14. F. Camps, J. Coll, A. Messeguer, et al., Synthesis, No. 2, 126 (1979).

    Google Scholar 

  15. E. A. Vdovtsova, Zh. Obshch. Khim.,5, 498 (1969).

    Google Scholar 

  16. I. N. Nazarov, L. A. Yanovskaya, B. P. Gusev, et al., Dokl. Akad. Nauk SSSR,114, 1029 (1957).

    Google Scholar 

  17. R. P. Lutz, H. A. Berg, and P. Y. Wang, J. Org. Chem.,41, No. 11, 2048 (1976).

    Google Scholar 

  18. H. Magari, H. Hirota, and T. Takanishi, J. Chem. Soc., Chem. Commun., No. 15, 1196 (1987).

    Google Scholar 

  19. G. H. Posner, Angew. Chem. Int. Ed.,17, 487 (1978).

    Google Scholar 

  20. A. McKillop and D. W. Young, Synthesis, 401, (1979).

  21. N. J. Turro, Tetrahedron,43, No. 7, 1589 (1987).

    Google Scholar 

  22. V. Ramamurthy, Tetrahedron,42, No. 21, 5753 (1986).

    Google Scholar 

  23. P. Laszlo (ed.), Preparative Chemistry Using Supported Reagents, Academic Press, New York (1987).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 835–842, April, 1991.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Pogrebnoi, S.I., Kal'yan, Y.B., Krimer, M.Z. et al. [3,3]-Sigmatropic rearrangements of the acetoacetates of allyl alcohols (Carroll reaction) and allylphenyl ethers (Claisen reaction) on the surface of adsorbents. Russ Chem Bull 40, 733–739 (1991). https://doi.org/10.1007/BF00958563

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00958563

Keywords

Navigation