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Regiospecific ene reaction of benzenesulfonyl chloride with linear isoprenoids

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

Conclusions

  1. 1.

    A regiospecific method is described for the terminal functionalization of linear isoprenoids, by carrying out the ene reaction with benzenesulfinyl chloride.

  2. 2.

    Some synthetic possibilities of the allyl sulfoxides thus obtained are examined, specifically the two-stage conversion of myrcene into E-β- (the alarm pheromone of certain species of mites) and Z-β-farnesenes.

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Literature cited

  1. A. M. Moiseenkov, V. A. Dragan, A. V. Shavnya, and V. V. Veselovskii, Izv. Akad. Nauk SSSR, Ser. Khim., 1692 (1986).

  2. E. E. Van Tamelen, Accounts Chem. Res.,1, 111 (1968).

    Google Scholar 

  3. N. Rabjohn, Organic Reactions, W. G. Dauben (ed.), John Wiley, New York (1976),24, p. 261.

    Google Scholar 

  4. V. V. Veselovskii, Z. G. Makarova, A. I. Lutsenko, et al., Izv. Akad. Nauk SSSR, Ser. Khim., 811 (1987).

  5. Y. Masaki, K. Hashimoto, and K. Kaji, Tetrahedron,40, 3481 (1984).

    Google Scholar 

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

    Google Scholar 

  7. G. Büchi and H. Wüest, Helv. Chim. Acta,50, 2440 (1967).

    Google Scholar 

  8. R. Chen and D. A. Rowand, J. Am. Chem. Soc.,102, 6609 (1980).

    Google Scholar 

  9. K. Sato, S. Inoue, A. Onishi, et al., J. Chem. Soc., Perkin Trans., 1, 761 (1981).

    Google Scholar 

  10. K. Mori, M. Waku, and M. Sakakibara, Tetrahedron,41, 2825 (1985).

    Google Scholar 

  11. Y. Masaki, K. Hashimoto, and K. Kaji, Tetrahedron Lett., 5123 (1978).

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

    Google Scholar 

  13. A. M. Moiseenkov, K. V. Lebedeva, and B. A. Cheskis, Usp. Khim.,53, 1709 (1984).

    Google Scholar 

  14. F. Muth, Methoden der Organischen Chemie (Houben-Weyl), E. Müller (ed.), Georg. Thieme Verlag, Stuttgart (1959), Vol. 9, p. 340.

    Google Scholar 

  15. H. Inouye, S. Ueda, S. Uesato, and K. Kobayashi, Chem. Pharm. Bull.,26, 3384 (1978).

    Google Scholar 

  16. Beilsteins Handbuch der Organischen Chemie, Vol. l, Part 2 (1973), p. 1133.

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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
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  2. V. A. Dragan
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  3. A. M. Moiseenkov
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Additional information

For previous communication, see [1].

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2787–2990, December, 1987.

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Veselovskii, V.V., Dragan, V.A. & Moiseenkov, A.M. Regiospecific ene reaction of benzenesulfonyl chloride with linear isoprenoids. Russ Chem Bull 36, 2583–2586 (1987). https://doi.org/10.1007/BF00957239

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  • DOI: https://doi.org/10.1007/BF00957239

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