[2+3]Cycloaddition reaction of a kinetically stabilized distibene with a nitrile oxide leading to the formation of a unique heterocyclic compound

Chemistry of Heterocyclic Compounds volume 42, pages1603–1609(2006)Cite this article

Abstract

The synthesis of a 1-oxa-5-aza-2,3-distibacyclopent-4-ene derivative by the [2+3]cycloaddition reaction of a kinetically stabilized distibene, BbtSb=SbBbt (Bbt = 2,6-bis[bis(trimethylsilyl)methyl]-4-[tris-(trimethylsilyl)methyl]phenyl), with MesCNO (Mes = mesityl) has been performed.

This is a preview of subscription content, access via your institution.

Access options

Buy single article

Instant access to the full article PDF.

34,95 €

Tax calculation will be finalised during checkout.

References

  1. 1.

    L. Weber, Chem. Rev., 92, 1839 (1992).

    Article  CAS  Google Scholar 

  2. 2.

    P. P. Power, Chem. Rev., 99, 3463 (1999).

    Article  CAS  Google Scholar 

  3. 3.

    N. Tokitoh, J. Organomet. Chem., 611, 217 (2000).

    Article  CAS  Google Scholar 

  4. 4.

    C. Jones, Coord. Chem. Rev., 215, 151 (2001).

    Article  CAS  Google Scholar 

  5. 5.

    M. Yoshifuji, I. Shima, N. Inamoto, K. Hirotsu, and T. Higuchi, J. Am. Chem. Soc., 103, 4587 (1981).

    Article  CAS  Google Scholar 

  6. 6.

    N. Tokitoh, Y. Arai, T. Sasamori, R. Okazaki, S. Nagase, H. Uekusa, and Y. Ohashi, J. Am. Chem. Soc., 120, 433 (1998).

    Article  CAS  Google Scholar 

  7. 7.

    N. Tokitoh, Y. Arai, R. Okazaki, and S. Nagase, Science, 277, 78 (1997).

    Article  CAS  Google Scholar 

  8. 8.

    M. Yoshifuji, K. Shibayama, N. Inamoto, K. Hirotsu, and T. Higuchi, J. Chem. Soc., Chem. Commun., 862 (1983).

  9. 9.

    M. Yoshifuji, K. Shibayama, I. Shima, and N. Inamoto, Phosphorus Sulfur, 18, 11 (1983).

    CAS  Google Scholar 

  10. 10.

    M. Yoshifuji, K. Ando, K. Shibayama, N. Inamoto, K. Hirotsu, and T. Higuchi, Angew. Chem., Int. Ed. Engl., 22, 418 (1983).

    Article  Google Scholar 

  11. 11.

    M. Yoshifuji, K. Shibayama, and N. Inamoto, Chem. Lett., 603 (1984).

  12. 12.

    M. Yoshifuji, K. Shibayama, and N. Inamoto, Heterocycles, 22, 681 (1984).

    CAS  Article  Google Scholar 

  13. 13.

    T. Sasamori, N. Takeda, and N. Tokitoh, J. Phys. Org. Chem., 16, 450 (2003)

    Article  CAS  Google Scholar 

  14. 14.

    T. Sasamori, E. Mieda, N. Takeda, and N. Tokitoh, Chem. Lett., 33, 104 (2004).

    Article  CAS  Google Scholar 

  15. 15.

    N. Tokitoh, T. Sasamori, and R. Okazaki, Chem. Lett., 27, 725 (1998).

    Article  Google Scholar 

  16. 16.

    T. Sasamori, E. Mieda, N. Takeda, and N. Tokitoh, Angew. Chem., Int. Ed., 44, 3717 (2005).

    Article  CAS  Google Scholar 

  17. 17.

    T. Sasamori, E. Mieda, N. Nagahora, N. Takeda, N. Takagi, S. Nagase, and N. Tokitoh, Chem. Lett., 34, 166 (2005).

    Article  CAS  Google Scholar 

  18. 18.

    T. Sasamori, E. Mieda, N. Nagahora, K. Sato, D. Shiomi, T. Takui, Y. Hosoi, Y. Furukawa, N. Takagi, S. Nagase, and N. Tokitoh, J. Am. Chem. Soc., 128, 12582 (2006).

    Google Scholar 

  19. 19.

    H. Bürger, R. Eujen, G. Becker, O. Mundt, and M. Westerhausen, C. Witthauer, J. Mol. Struct., 98, 265 (1983).

    Article  Google Scholar 

  20. 20.

    S. Nagase, in The Chemistry of Organic Arsenic, Antimony, and Bismuth Compounds, S. Patai (Ed), Wiley, New York, 1994, p. 1.

    Google Scholar 

  21. 21.

    P. Pyykkö, Chem. Rev., 88, 563 (1988).

    Article  Google Scholar 

  22. 22.

    S. Nagase, S. Suzuki, and T. Kurakake, J. Chem. Soc., Chem. Commun., 1724 (1990).

  23. 23.

    C. Grundmann and J. M. Dean, J. Org. Chem., 30, 2809 (1965).

    Article  CAS  Google Scholar 

  24. 24.

    G. Sheldrick, Acta Crystallogr., A46, 467 (1990).

    CAS  Google Scholar 

  25. 25.

    G. Sheldrick, SHELX-97_Program for Crystal Structure Solution and the Refinement of Crystal Structures, Institüt für Anorganische Chemie der Universität Göttingen, Tammanstrasse 4, D-3400 Göttingen, Germany (1997).

    Google Scholar 

  26. 26.

    Gaussian 03 Program, Revision A.11, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, P. Salvador, J. J. Dannenberg, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, and J. A. Pople, Gaussian, Inc., Pittsburgh PA, 2001.

    Google Scholar 

  27. 27.

    W. R. Wadt and P. J. Hay, J. Chem. Phys., 82, 284 (1985).

    Article  CAS  Google Scholar 

  28. 28.

    C. E. Check, T. O. Faust, J. M. Bailey, B. J. Wright, T. M. Gilbert, and L. S. Sunderlin, J. Phys. Chem., A, 105, 8111 (2001).

    Article  CAS  Google Scholar 

Download references

Author information

Affiliations

  1. Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto, 611-0011, Japan

    T. Sasamori, E. Mieda, N. Nagahora & N. Tokitoh

Authors
  1. T. Sasamori
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. Mieda
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. N. Nagahora
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. N. Tokitoh
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to N. Tokitoh.

Additional information

Dedicated to Prof. Dr. E. Lukevics on the occasion of his 70th birthday

__________

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1880–1887, December, 2006.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Sasamori, T., Mieda, E., Nagahora, N. et al. [2+3]Cycloaddition reaction of a kinetically stabilized distibene with a nitrile oxide leading to the formation of a unique heterocyclic compound. Chem Heterocycl Compd 42, 1603–1609 (2006). https://doi.org/10.1007/s10593-006-0284-y

Download citation

Keywords

  • distibene
  • nitrile oxide
  • 1-oxa-5-aza-2,3-distibacylopent-4-ene
  • cycloaddition
  • X-ray crystallographic analysis