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Russian Chemical Bulletin

, Volume 65, Issue 1, pp 195–199 | Cite as

Regioselective [6π+2π] cycloaddition of 1,2-dienes to 7-substituted 1,3,5-cycloheptatrienes catalyzed by Ti(acac)2Cl2—Et2AlCl

  • G. N. Kadikova
  • D. I. Kolokoltsev
  • E. S. Meshcheryakova
  • V. A. D’yakonov
  • U. M. Dzhemilev
Full Articles
  • 31 Downloads

Abstract

A reaction of 7-alkyl-, 7-allyl-, 7-phenyl-1,3,5-cycloheptatrienes with 1,2-dienes in the presence of the two-component catalytic system Ti(acac)2Cl2—Et2AlCl, which led to the formation of practically important substituted endo-bicyclo[4.2.1]nona-2,4-dienes in up to 90% yields, was accomplished for the first time.

Keywords

7-substituted 1,3,5-cycloheptatrienes homogeneous metal complex catalysis cycloaddition 1,2-dienes bicyclo[4.2.1]nona-2,4-diene diethylaluminum chloride titanum 

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References

  1. 1.
    N. A. Petasis, M. A. Patane, Tetrahedron, 1992, 48, 5757.CrossRefGoogle Scholar
  2. 2.
    Z.-X. Yu, Y. Wang, Y. Wang, Chem. Asian J., 2010, 5, 1072.CrossRefGoogle Scholar
  3. 3.
    M. Lautens, W. Klute, W. Tam, Chem. Rew., 1996, 96, 49..CrossRefGoogle Scholar
  4. 4.
    K. Mach, H. Antropiusova, P. Sedmera, V. Hanus, F. Turecek, J. Chem. Soc., Chem. Commun., 1983, 805.Google Scholar
  5. 5.
    K. Mach, H. Antropiusova, L. Petrusova, V. Hanus, F. Turecek, Tetrahedron, 1984, 40, 3295.CrossRefGoogle Scholar
  6. 6.
    S. Ozkar, H. Kurz, D. Neugebauer, C.G. Kreiter, J. Organomet. Chem., 1978, 160, 115.CrossRefGoogle Scholar
  7. 7.
    C. G. Kreiter, H. Kurz, Chem. Ber., 1983, 116, 1494.CrossRefGoogle Scholar
  8. 8.
    I. Fischler, F.-W. Grevels, J. Leitich, S. Ozkar, Chem. Ber., 1991, 124, 2857.CrossRefGoogle Scholar
  9. 9.
    J. H. Rigby, Tetrahedron, 1999, 55, 4521.CrossRefGoogle Scholar
  10. 10.
    J. H. Rigby, S. B. Laurent, Z. Kamal, M. J. Heeg, J. Org. Lett., 2008, 10, 5609.CrossRefGoogle Scholar
  11. 11.
    J. H. Rigby, L. W. Mann, B. J. Myers, Tetrahedron Lett., 2001, 42, 8773.CrossRefGoogle Scholar
  12. 12.
    K. Chaffee, P. Huo, J. B. Sheridan, A. Barbieri, A. Aistars, R. A. Lalancette, R. L. Ostrander, A. L. Rheingold, J. Am. Chem. Soc., 1995, 117, 1900.CrossRefGoogle Scholar
  13. 13.
    M. Achard, A. Tenaglia, G. Buono, Organic Lett., 2005, 7, 2353.CrossRefGoogle Scholar
  14. 14.
    G. Hilt, A. Paul, C. Hengst, Synthesis, 2009, 19, 3305.CrossRefGoogle Scholar
  15. 15.
    H. Clavier, K. L. Jeune, I. Riggi, A. Tenaglia, G. Buono, J. Org. Lett., 2011, 13, 308.CrossRefGoogle Scholar
  16. 16.
    J. H. Rigby, S.V. Cuisiat, J. Org. Chem., 1993, 58, 6286.CrossRefGoogle Scholar
  17. 17.
    J. H. Rigby, N. M. Niyaz, K. Short, M. J. Heeg, J. Org. Chem., 1995, 60, 7720.CrossRefGoogle Scholar
  18. 18.
    J. H. Rigby, N. M. Niyaz, B. Bazin, Tetrahedron, 2002, 58, 4879.CrossRefGoogle Scholar
  19. 19.
    V. A. D’yakonov, O. A. Trapeznikova, A. de Meijere, U. M. Dzhemilev, Chem. Rev., 2014, 114, 5775.CrossRefGoogle Scholar
  20. 20.
    V. A. D’yakonov, G. N. Kadikova, L. M. Khalilov, U. M. Dzhemilev, Russ. Chem. Bull. (Int. Ed.), 2011, 60, 499 [Izv. Akad. Nauk, Ser. Khim., 2011, 489].CrossRefGoogle Scholar
  21. 21.
    V. A. D’yakonov, G. N. Kadikova, U. M. Dzhemilev, Tetrahedron Lett., 2011, 52, 2780.CrossRefGoogle Scholar
  22. 22.
    U. M. Dzhemilev, G. N. Kadikova, D. I. Kolokoltsev, V. A. D’yakonov, Tetrahedron, 2013, 69, 4609.Google Scholar
  23. 23.
    V. A. D’yakonov, D. I. Kolokoltsev, G. N. Kadikova, U. M. Dzhemilev, Russ. Chem. Bull. (Int. Ed.), 2013, 62, 1016 [Izv. Akad. Nauk, Ser. Khim., 2013, 1015].CrossRefGoogle Scholar
  24. 24.
    V. A. D’yakonov, G. N. Kadikova, L. M. Khalilov, U. M. Dzhemilev, Russ. Chem. Bull. (Int. Ed.), 2011, 60, 182 [Izv. Akad. Nauk, Ser. Khim., 2011, 174].CrossRefGoogle Scholar
  25. 25.
    V. A. D’yakonov, G. N. Kadikova, L. M. Khalilov, U. M. Dzhemilev, Russ. J. Org. Chem., 2013, 49, 1139 [Zh. Org. Khim., 2013, 49, 1157].CrossRefGoogle Scholar
  26. 26.
    A. J. Gordon, R. A. Ford, The Chemist’s Companion, J. Wiley and Sons, New York—London—Sydney—Toronto, 1972, 300 pp.Google Scholar
  27. 27.
    G. M. Sheldrick, Acta Cryst., 2008, A64, 112.CrossRefGoogle Scholar
  28. 28.
    U. M. Dzhemilev, N. R. Popod’ko, E. V. Kozlova, Metallokompleksnyi kataliz v organicheskom sinteze [Metal Complex Catalysis in Organic Synthesis], Khimiya, Moscow, 1999, 631 pp. (in Russian).Google Scholar
  29. 29.
    L. Brandsma, Synthesis of Acetylenes, Allenes and Cumulenes: Methods and Techniques, Elsevier Acad. Press, 2004, 470 pp.Google Scholar
  30. 30.
    K. Conrow, J. Am. Chem. Soc., 1961, 83, 2343.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2016

Authors and Affiliations

  • G. N. Kadikova
    • 1
  • D. I. Kolokoltsev
    • 1
  • E. S. Meshcheryakova
    • 1
  • V. A. D’yakonov
    • 1
  • U. M. Dzhemilev
    • 1
  1. 1.Institute of Petrochemistry and CatalysisRussian Academy of SciencesUfaRussian Federation

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