Skip to main content
SpringerLink
Log in

Synthesis of E/Z-sesquilavandulols from the product of the ene reaction of lavandulyl acetate with phenylsulfinyl chloride

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

Abstract

The ene reaction of (±)-lavandulyl acetate with PhSOCl catalyzed by ZnCl2 proceeds highly selectively at the isopropylidene fragment of this molecule to give the corresponding allyl sulfoxide. The sulfoxide-sulfenate rearrangement of this product and its one-step conversion to a mixture of racemic E/Z-sesquilavandulols were studied.

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

Literature cited

  1. A. M. Moiseenkov, V. A. Dragan, V. A. Koptenkova, and V. V. Veselovskii (Veselovsky), Synthesis, 814 (1987).

  2. V. V. Veselovskii, V. A. Dragan, and A. M. Moiseenkov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 12, 2787 (1987).

    Google Scholar 

  3. Beilsteins Handbuch der Organischen Chemie, Vol. 1 (1958), p. 2014; Vol. 2 (1960), p. 301.

  4. D. A. Evans and G. C. Andrews, Accounts Chem. Res.,7, 147 (1974).

    Google Scholar 

  5. Z. Horii, Y. Ozaki, K. Nagao, and S.-W. Kim, Tetrahedron Lett., 5015 (1978).

  6. K. H. Kubeczka, C. Schmaus, and V. Formacek, Progress in Essential Oil Research. Proceedings of the Sixteenth International Symposium on Essential Oils, Berlin (1986), p. 271; Chem. Abstr.,105, 120461j (1986).

  7. A. M. Moiseenkov, V. A. Koptenkova, and V. V. Veselovskii, Dokl. Akad. Nauk SSSR,299 1402 (1988).

    Google Scholar 

  8. V. V. Veselovskii, V. A. Koptenkova, and A. M. Moiseenkov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 372 (1989).

    Google Scholar 

  9. Y. Masaki, K. Sakuma, and K. Kaji, J. Chem. Soc., Perkin Trans. 1, 1171 (1985).

    Google Scholar 

  10. F. Muth, in: E. Muller (ed.), Methoden der Organischen Chemie (Houben-Weyl), Vol. 9, Georg Thieme Verlag, Stuttgart (1955), p. 340.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    V. V. Veselovskii, V. A. Dragan & A. M. Moiseenkov

Authors
  1. V. V. Veselovskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. A. Dragan
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. M. Moiseenkov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1906–1908, August, 1990.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Veselovskii, V.V., Dragan, V.A. & Moiseenkov, A.M. Synthesis of E/Z-sesquilavandulols from the product of the ene reaction of lavandulyl acetate with phenylsulfinyl chloride. Russ Chem Bull 39, 1734–1736 (1990). https://doi.org/10.1007/BF00961515

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00961515

Keywords

Search

Navigation