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

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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.

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References

  1. N. A. Petasis, M. A. Patane, Tetrahedron, 1992, 48, 5757.

    Article  CAS  Google Scholar 

  2. Z.-X. Yu, Y. Wang, Y. Wang, Chem. Asian J., 2010, 5, 1072.

    Article  CAS  Google Scholar 

  3. M. Lautens, W. Klute, W. Tam, Chem. Rew., 1996, 96, 49..

    Article  CAS  Google Scholar 

  4. K. Mach, H. Antropiusova, P. Sedmera, V. Hanus, F. Turecek, J. Chem. Soc., Chem. Commun., 1983, 805.

    Google Scholar 

  5. K. Mach, H. Antropiusova, L. Petrusova, V. Hanus, F. Turecek, Tetrahedron, 1984, 40, 3295.

    Article  CAS  Google Scholar 

  6. S. Ozkar, H. Kurz, D. Neugebauer, C.G. Kreiter, J. Organomet. Chem., 1978, 160, 115.

    Article  Google Scholar 

  7. C. G. Kreiter, H. Kurz, Chem. Ber., 1983, 116, 1494.

    Article  CAS  Google Scholar 

  8. I. Fischler, F.-W. Grevels, J. Leitich, S. Ozkar, Chem. Ber., 1991, 124, 2857.

    Article  CAS  Google Scholar 

  9. J. H. Rigby, Tetrahedron, 1999, 55, 4521.

    Article  CAS  Google Scholar 

  10. J. H. Rigby, S. B. Laurent, Z. Kamal, M. J. Heeg, J. Org. Lett., 2008, 10, 5609.

    Article  CAS  Google Scholar 

  11. J. H. Rigby, L. W. Mann, B. J. Myers, Tetrahedron Lett., 2001, 42, 8773.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  13. M. Achard, A. Tenaglia, G. Buono, Organic Lett., 2005, 7, 2353.

    Article  CAS  Google Scholar 

  14. G. Hilt, A. Paul, C. Hengst, Synthesis, 2009, 19, 3305.

    Article  Google Scholar 

  15. H. Clavier, K. L. Jeune, I. Riggi, A. Tenaglia, G. Buono, J. Org. Lett., 2011, 13, 308.

    Article  CAS  Google Scholar 

  16. J. H. Rigby, S.V. Cuisiat, J. Org. Chem., 1993, 58, 6286.

    Article  CAS  Google Scholar 

  17. J. H. Rigby, N. M. Niyaz, K. Short, M. J. Heeg, J. Org. Chem., 1995, 60, 7720.

    Article  CAS  Google Scholar 

  18. J. H. Rigby, N. M. Niyaz, B. Bazin, Tetrahedron, 2002, 58, 4879.

    Article  CAS  Google Scholar 

  19. V. A. D’yakonov, O. A. Trapeznikova, A. de Meijere, U. M. Dzhemilev, Chem. Rev., 2014, 114, 5775.

    Article  Google Scholar 

  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].

    Article  Google Scholar 

  21. V. A. D’yakonov, G. N. Kadikova, U. M. Dzhemilev, Tetrahedron Lett., 2011, 52, 2780.

    Article  Google Scholar 

  22. U. M. Dzhemilev, G. N. Kadikova, D. I. Kolokoltsev, V. A. D’yakonov, Tetrahedron, 2013, 69, 4609.

  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].

    Article  Google Scholar 

  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].

    Article  Google Scholar 

  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].

    Article  Google Scholar 

  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. G. M. Sheldrick, Acta Cryst., 2008, A64, 112.

    Article  Google Scholar 

  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. L. Brandsma, Synthesis of Acetylenes, Allenes and Cumulenes: Methods and Techniques, Elsevier Acad. Press, 2004, 470 pp.

    Google Scholar 

  30. K. Conrow, J. Am. Chem. Soc., 1961, 83, 2343.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, 141 prosp. Oktyabrya, 450075, Ufa, Russian Federation

    G. N. Kadikova, D. I. Kolokoltsev, E. S. Meshcheryakova, V. A. D’yakonov & U. M. Dzhemilev

Authors
  1. G. N. Kadikova
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  2. D. I. Kolokoltsev
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  3. E. S. Meshcheryakova
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  4. V. A. D’yakonov
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  5. U. M. Dzhemilev
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Correspondence to V. A. D’yakonov.

Additional information

Based on the Materials of Conference Molecular Complexity in Modern Chemistry (September 13—19, 2014, Moscow, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0195—0199, January, 2016.

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Kadikova, G.N., Kolokoltsev, D.I., Meshcheryakova, E.S. et al. Regioselective [6π+2π] cycloaddition of 1,2-dienes to 7-substituted 1,3,5-cycloheptatrienes catalyzed by Ti(acac)2Cl2—Et2AlCl. Russ Chem Bull 65, 195–199 (2016). https://doi.org/10.1007/s11172-016-1283-5

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  • DOI: https://doi.org/10.1007/s11172-016-1283-5

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