Russian Chemical Bulletin

, Volume 60, Issue 8, pp 1628–1632 | Cite as

The Cp2ZrCl2-catalyzed cycloalumination of functionally substituted olefins with triethylaluminum

  • I. R. Ramazanov
  • R. N. Kadikova
  • U. M. Dzhemilev
Full Articles


Reactions of functionally substituted olefins (allylamines, sulfides and ethers, homoallylic alcohols and amines, as well as vinyl ethers) with Et3Al in the presence of Cp2ZrCl2 as a catalyst were studied. Cycloalumination of allylamines occurs with high regioselectivity to furnish after subsequent deuterolysis 4-deutero-2-(deuteromethyl)butyl-substituted amines. Cycloalumination of alkyl allyl sulfide is accompanied by a side process of the C-S bond cleavage. In the case of allyl and vinyl ethers, no cycloalumination products are formed under the reaction conditions. However, the reactions with homoallylic alcohol and amine after deuterolysis gave the corresponding dideutero-containing compounds in good yields.

Key words

cycloalumination functionally substituted olefins aluminacyclopentanes 


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  1. 1.
    U. M. Dzhemilev, A. G. Ibragimov, A. P. Zolotarev, R. R. Muslukhov, G. A. Tolstikov, Izv. Akad. Nauk SSSR, Ser. Khim., 1989, 207 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1989, 38, 194].Google Scholar
  2. 2.
    U. M. Dzhemilev, A. G. Ibragimov, A. P. Zolotarev, Mendeleev Commun., 1992, 135.Google Scholar
  3. 3.
    G. Dawson, C. A. Durrant, G. G. Kirk, R. J. Whitby, R. V. H. Jones, M. C. H. Standen, Tetrahedron Lett., 1997, 38, 2335.CrossRefGoogle Scholar
  4. 4.
    U. M. Dzhemilev, A. G. Ibragimov, Usp. Khim., 2000, 69, 134 [Russ. Chem. Rev. (Engl. Transl.), 2000, 69, 121].Google Scholar
  5. 5.
    I. R. Ramazanov, R. N. Kadikova, U. M. Dzhemilev, Izv. Akad. Nauk, Ser. Khim., 2011, 96 [Russ. Chem. Bull., Int. Ed., 2011, 60, 99].Google Scholar
  6. 6.
    E.-I. Negishi, D. Y. Kondakov, D. Choueiry, K. Kasai, T. Takahashi, J. Am. Chem. Soc., 1996, 118, 9577.CrossRefGoogle Scholar
  7. 7.
    C. J. Rousset, D. R. Swanson, F. Lamaty, E. Negishi, Tetrahedron Lett., 1989, 30, 5105.CrossRefGoogle Scholar
  8. 8.
    A. M. Schmidt, P. Eilbracht, J. Org. Chem., 2005, 70, 5528.CrossRefGoogle Scholar
  9. 9.
    B. V. S. K. Rao, R. Subbarao, J. Am. Oil Chem. Soc., 1991, 68, 646.CrossRefGoogle Scholar
  10. 10.
    I. H. S. Estevama, M. F. da Silvaa, L. W. Bieber, Tetrahedron Lett., 2005, 46, 7601.CrossRefGoogle Scholar
  11. 11.
    SDBSWeb: (National Institute of Advanced Industrial Science and Technology, 13.12.2010).

Copyright information

© Springer-Verlag 2011

Authors and Affiliations

  • I. R. Ramazanov
    • 1
  • R. N. Kadikova
    • 1
  • U. M. Dzhemilev
    • 1
  1. 1.Institute of Petrochemistry and CatalysisRussian Academy of SciencesUfaRussian Federation

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