Russian Journal of Organic Chemistry

, Volume 49, Issue 5, pp 669–671 | Cite as

Fe-catalyzed synthesis of (4E)-tridec-4-en-1-yl acetate, sex pheromone of tomato pinworm (Keiferia lycopersicella)

  • R. N. Shakhmaev
  • A. Sh. Sunagatullina
  • V. V. Zorin


Starting with industrially available 1,3-dichloropropene a stereoselective process was developed for the preparation of (4E)-tridec-4-en-1-yl acetate, sex pheromone of tomato pinworm (Keiferia lycopersicella) using in the key stage the Fe-catalyzed cross-coupling of ethyl (4E)-5-chloropent-4-enoate with octylmagnesium bromide.


Oily Substance Aluminum Hydride Lithium Aluminum Hydride Anhydrous Ether Claisen Rearrangement 
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  1. 1.
    Charlton, R.E., Wyman, J.A., McLaughlin, J.R., Du, J.-W., and Roelofs, W.L. J. Chem. Ecol., 1991, vol. 17, p. 175.CrossRefGoogle Scholar
  2. 2.
    Patterson, J.W., Synthesis., 1985, p. 337.Google Scholar
  3. 3.
    Fukumoto, T. and Yamamoto, A., Japan Patent 2101028, 1990; Chem. Abstr., 1990, vol. 113, 112635t.Google Scholar
  4. 4.
    Melikyan, G.G., Aslanyan, G.Kh., Atanesyan, K.A., Mkrtchyan, D.A., and Badanyan, Sh.O., Khim. Polim. Soedin., 1990, p. 102.Google Scholar
  5. 5.
    Bikulova, L.M., Verba, G.G., and Abduvakhabov, A.A., Khim. Polim. Soedin., 1991, p. 444.Google Scholar
  6. 6.
    Odinokov, V.N., Vakhidov, R.R., Shakhmaev, R.N., and Gil’vanova, N.V., Khim. Polim. Soedin., 1995, p. 490.Google Scholar
  7. 7.
    Moiseenkov, A.M., Czeskis, B.A., Ivanova, N.M., and Nefedov, O.M., J. Chem. Soc., Perkin Trans. I, 1991, p. 2639.Google Scholar
  8. 8.
    Mitchener, J.P. Jr., Thomas, J.C., and Ogle, C.A., Main Group, Met. Chem., 1999, vol. 22, p. 435.CrossRefGoogle Scholar
  9. 9.
    Seufert, W., Buschamann, E., Becker, R., Seppelt, W., and Macken-roth, W., German Patent 4006919, 1991; Chem. Abstr., 1991, vol. 115, 255619n.Google Scholar
  10. 10.
    Sunagatullina, A.Sh., Shakhmaev, R.N., and Zorin, V.V., Bash. Khim. Zh., 2012, vol. 19, p. 5.Google Scholar
  11. 11.
    Krapcho, A.P., Synthesis, 1982, p. 805.Google Scholar
  12. 12.
    Odinokov, V.N., Bakeeva, R.S., Galeeva, R.I., Akhunova, V.R., Mukhtarov, Ya.G., Tolstikov, G.A., Khalilov, L.M., and Panasenko, A.A., Zh. Org. Khim., 1979, vol. 15, p. 2017.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2013

Authors and Affiliations

  • R. N. Shakhmaev
    • 1
  • A. Sh. Sunagatullina
    • 1
  • V. V. Zorin
    • 1
  1. 1.Ufa State Oil Engineering UniversityUfaRussia

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