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One-step cyclopropanation of alkynes with diiodomethane and triethylaluminum

Russian Chemical Bulletin volume 50, pages 1406–1409 (2001)Cite this article

Abstract

Cyclopropanation of mono- and dialkyl-substituted alkynes under the action of CH2I2 and Et3Al afforded the corresponding 1-alkyl- and 1,2-dialkyl-substituted 1,2-diethylcyclopropanes in 65—80% yields.

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References

  1. D. B. Miller, Tetrahedron Lett., 1964, 17, 989.

    Google Scholar 

  2. K. Maruoka, Y. Fukutani, and H. Yamamoto, J. Org. Chem., 1985, 50, 4412.

    Google Scholar 

  3. J. M. Russo and W. A. Price, J. Org. Chem., 1993, 58, 3589.

    Google Scholar 

  4. D. Li, H.-q. Zhou, S. Dakoji, I. Shin, E. Oh, and H.-W. Liu, J. Am. Chem. Soc., 1998, 120, 2008.

    Google Scholar 

  5. U. M. Dzhemilev, A. G. Ibragimov, I. R. Ramazanov, M. P. Luk'yanova, A. Z. Sharipova, and L. M. Khalilov, Izv. Akad. Nauk, Ser. Khim., 2000, 1092 [Russ. Chem. Bull., Int. Ed., 2000, 49, 1086].

    Google Scholar 

  6. H. Hoberg, Lieb. Ann., 1962, 656, 1.

    Google Scholar 

  7. A. T. Stoll and E. Negishi, Tetrahedron Lett., 1985, 26, 5671.

    Google Scholar 

  8. R. Schimpf and P. Heimbach, Chem. Ber., 1970, 103, 2122.

    Google Scholar 

  9. D. E. Van Horn and E. Negishi, J. Am. Chem. Soc., 1978, 100, 2252.

    Google Scholar 

  10. U. M. Dzhemilev, A. G. Ibragimov, and A. P. Zolotarev, Mendeleev Commun., 1992, 4, 135.

    Google Scholar 

  11. U. M. Dzhemilev, A. G. Ibragimov, I. R. Ramazanov, M. P. Luk'yanova, and A. Z. Sharipova, Izv. Akad. Nauk, Ser. Khim., 2001, 465 [Russ. Chem. Bull., Int. Ed., 2001, 50, 484].

    Google Scholar 

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Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis, Bashkortostan Republic Academy of Sciences and Ufa Scientific Center of the Russian Academy of Sciences, 141 prosp. Oktyabrya, 450075, Ufa, Russian Federation

    I. R. Ramazanov, M. P. Luk"yanova, A. Z. Sharipova, A. G. Ibragimov & U. M. Dzhemilev

  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    O. M. Nefedov

Authors
  1. I. R. Ramazanov
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  2. M. P. Luk"yanova
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  3. A. Z. Sharipova
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  4. A. G. Ibragimov
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  5. U. M. Dzhemilev
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  6. O. M. Nefedov
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Ramazanov, I.R., Luk"yanova, M.P., Sharipova, A.Z. et al. One-step cyclopropanation of alkynes with diiodomethane and triethylaluminum. Russian Chemical Bulletin 50, 1406–1409 (2001). https://doi.org/10.1023/A:1012733023065

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  • DOI: https://doi.org/10.1023/A:1012733023065

  • alkynes
  • cyclopropanes
  • cyclopropanation