Skip to main content
SpringerLink
Log in

Ene-type reaction of trisubstituted monoterpene alkenes with methyl sulfite and thionyl chloride

  • Organic Chemistry
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Trisubstituted methylalkenes react with methyl sulfite at ∼25°C in the presence of BF3 · Et2O in the ene-type fashion to give the corresponding methallyl sulfinates. Such compounds can also be prepared under considerably milder conditions by the Et2AlCl-catalyzed reaction of thionyl chloride with mono- and dienes followed by methanolysis of intermediate alkyl sulfinyl chlorides. These reactions represent a new method for terminal functionalization of linear isoprenoids.

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. O.Vichterle and Ya.Rocek,Coll,Czech.Chem.Commun., 1954,19, 282.

    Google Scholar 

  2. P.E.Peterson, R. Brockington, and M. Dunham,J.Am.Chem. Soc., 1975,97, 3517.

    Google Scholar 

  3. M.M.Rogic and D.Masilamani,J.Am.Chem.Soc., 1977,99, 5219.

    Google Scholar 

  4. E.J.Corey and T.A.Engler,Tetrahedron Lett, 1984,25, 149.

    Google Scholar 

  5. I.M.Zax, E.V.Polunin, and A.M.Moiseenkov,Izv.Akad. Nauk SSSR. Ser.Khim., 1984, 2799 [Bull.Acad.Sci. USSR, Div.Chem.Sci., 1984,33, 2564].

  6. A.M.Moiseenkov, A.N.Rechitskii, E.V.Polunin, and O.N.Yudina,Izv.Akad. Nauk SSSR. Ser.Khim., 1985, 1820 [Bull.Acad.Sci. USSR, Div.Chem.Sci., 1985,34, 1667].

  7. J.Drabowicz, P.Kielbasinski, and M.Mikolajczyk,The Chemistry of Sulfones and Sulfoxides, Eds. S.Patai, Z.Rappoport, and C.J.M. Stirling, John Wiley & Sons, Ltd., 1988, Chapter 8, p.233.

  8. V.V.Veselovskii, V.A.Dragan, and A.M.Moiseenkov,Izv. Akad. Nauk SSSR. Ser.Khim., 1987, 2787 [Bull. Acad.Sci. USSR, Div.Chem.Sci., 1984,36, 2583].

  9. V.V.Veselovskii, V.A.Dragan, and A.M.Moiseenkov,Izv. Akad.Nauk SSSR. Ser. Khim., 1990, 1906 [Bull. Acad.Sci. USSR, Div.Chem.Sci., 1990,39, 2094].

  10. V.A.Dragan, V.V.Veselovskii, E.D.Daeva, and A.M.Moiseenkov,Izv.Akad.Nauk SSSR. Ser.Khim., 1991, 857 [Bull.Acad.Sci. USSR, Div.Chem.Sci., 1991,40, 754].

  11. A.M.Moiseenkov, V.A.Dragan, and V.V. Veselovskii,Izv. Akad.Nauk SSSR. Ser.Khim., 1989, 365 [Bull.Acad.Sci. USSR. Div.Chem.Sci., 1989,38, 314].

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. N.D.Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 117913, Moscow, Russian Federation

    V. A. Dragan & A. M. Moiseenkov

Authors
  1. V. A. Dragan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. M. Moiseenkov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Deceased Nov.1, 1992.

Translated fromIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 1, pp. 105–107, January, 1993.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dragan, V.A., Moiseenkov, A.M. Ene-type reaction of trisubstituted monoterpene alkenes with methyl sulfite and thionyl chloride. Russ Chem Bull 42, 95–97 (1993). https://doi.org/10.1007/BF00699983

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00699983

Key words

Search

Navigation