Two-step cis-C5-homologization of prenyl halides

  • A. M. Moiseenkov
  • E. V. Polunin
Organic Chemistry

Conclusions

  1. 1.

    A study was carried out on the desulfonylation of nerol and Z,E-farnesol hydroxysulfonamides and conditions were found for the removal of the sulfonamide group without migration of the C=C bond and obtaining the corresponding oligoprenols.

     
  2. 2.

    The electrochemical desulfonylation of nerylsulfonamide leads to isogeraniol.

     
  3. 3.

    The treatment of the morpholide of l-phenylthio-4-hydroxy-2-methylbut-2Z-ene-1-sulfonic acid with 2 equivalents of Li in NH3 at -70‡C leads to loss of the phenylsulfide group while 3-methylbut-2-en-1-ol is formed when using excess Li.

     

Keywords

Sulfonamide Migration Halide Sulfonamide Group Prenyl 

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Literature cited

  1. 1.
    A. M. Moiseenkov, E. V. Polunin, and A. V. Semenovskii (Semenovsky), Angew. Chem.,93, 1122 (1981).Google Scholar
  2. 2.
    H. O. Huisman, Pure Appl. Chem.,49, 1307 (1977).Google Scholar
  3. 3.
    G. Cainelli and G. Cardillo, Accounts Chem. Res.,14, 89 (1981).Google Scholar
  4. 4.
    T. Nakai, H. Shiono, and M. Okawara, Tetrahedron Lett., 4027 (1975).Google Scholar
  5. 5.
    M. Julia, D. Uguen, and A. Callipolitis, Bull. Soc. Chim. France, 519 (1976).Google Scholar
  6. 6.
    M. Kodama, S. Yokoo, H. Yamada, and S. Ito, Tetrahedron Lett., 3121 (1978).Google Scholar
  7. 7.
    K. Sato, S. Inoue, A. Onishi, N. Uchida, and N. Minowa, J. Chem. Soc., Perkin Trans. I, 761 (1981).Google Scholar
  8. 8.
    K. Shimada, M. Kodama, and S. Ito, Tetrahedron Lett., No. 22, 4275 (1981).Google Scholar
  9. 9.
    K. Sato, O. Miyamoto, S. Inoue, T. Kobayashi, and F. Furusawa, Chem. Lett., 1711 (1981).Google Scholar
  10. 10.
    Y. Fujita, M. Ishiguro, T. Onishi, and T. Nishida, Bull. Chem. Soc. Jpn.,55, 1325 (1982).Google Scholar
  11. 11.
    E. V. Polunin, A. M. Moiseenkov, and A. V. Semenovskii, Izv. Akad. Nauk SSSR, Ser. Khim., 1354 (1981).Google Scholar
  12. 12.
    U. Vogeli and W. von Philipsborn, Org. Magn. Reson.,7, 617 (1975).Google Scholar
  13. 13.
    C. Nishino and W. S. Bowers, Tetrahedron,32, 2875 (1976).Google Scholar
  14. 14.
    B. M. Trost, H. C. Arndt, P. E. Strege, and T. R. Verhoeven, Tetrahedron Lett., 3477 (1976).Google Scholar
  15. 15.
    T. Kato, H. Takayanagi, T. Uyehara, and Y. Kitahara, Chem. Lett., 1009 (1977).Google Scholar
  16. 16.
    N. S. Poonia and A. V. Bajaj, Chem. Rev.,79, 389 (1979).Google Scholar
  17. 17.
    E. W. Erman, J. Am. Chem. Soc.,89, 3828 (1967).Google Scholar
  18. 18.
    Altaian, L. Ash, and S. Marson, Synthesis, 129 (1974).Google Scholar
  19. 19.
    R. H. Bedoukian and J. Wollinsky, J. Org. Chem.,40, 2154 (1975).PubMedGoogle Scholar

Copyright information

© Plenum Publishing Corporation 1984

Authors and Affiliations

  • A. M. Moiseenkov
    • 1
  • E. V. Polunin
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

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