Skip to main content
Log in

1,3-Dipolar cycloaddition reaction of nitrone η6-(arene)chromium tricarbonyl complexes with styrene and η6-(styrene)chromium tricarbonyl

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The products of 1,3-dipolar cycloaddition of the nitrone-type η6-(arene)chromium tricarbonyl complexes (CO)3CrC6H5CH=N+(O)R, where R = Me, Ph, But, with styrene and η6-(styrene)chromium tricarbonyl were obtained and characterized by a combination of physicochemical methods. This type of reactions proceeded with very high regio- and stereoselectivity to exclusively form cis-2,3,5-tri-substituted isoxazolidines.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. M. Rosillo, G. Dominguez, J. Perez-Castells, Chem. Soc. Rev., 2007, 36, 1589.

    Article  CAS  Google Scholar 

  2. C. Mukai, I. J. Kim, W. J. Cho, M. Hanaoka, Tetrahedron Lett., 1990, 31, 6893.

    Article  CAS  Google Scholar 

  3. C. Mukai, I. J. Kim., W. J. Cho, M. Kido, M. Hanaoka, J. Chem. Soc. Perkin Trans., 1, 1993, 2495.

    Google Scholar 

  4. C. Baldoli, S. Maiorana, E. Licandro, G. Zinzalla, M. Lanfranchi, A. Tiripicchio, Tetrahedron Asymmetry, 2001, 12, 2159.

    Article  CAS  Google Scholar 

  5. P. N. Confalone, E. M. Huie, Org. React., 1988, 36, 1.

    CAS  Google Scholar 

  6. R. Huisgen, R. Grashey, H. Hauk, H. Seidl, Chem. Ber., 1968, 101, 2548.

    Article  CAS  Google Scholar 

  7. R. Huisgen, H. Hauk, R. Grashey, H. Seidl, Chem. Ber., 1968, 101, 2568.

    Article  CAS  Google Scholar 

  8. A. N. Artemov, E. V. Sazonova, E. A. Mavrina, N. Yu. Zarovkina, Russ. Chem. Bull. (Int. Ed.), 2012, 61, 2076 [Izv. Akad. Nauk, Ser. Khim., 2012, 11, 2059].

    Article  CAS  Google Scholar 

  9. K. Heusler, P. Wieland, Ch. Meystre, Org. Synth., 1973, 5, 1124.

    Google Scholar 

  10. W. D. Emmons, J. Am. Chem. Soc., 1957, 79, 5739.

    Article  CAS  Google Scholar 

  11. M. D. Raush, G. A. Moser, E. S. Zaiko, A. L. Lipman, J. Organomet. Chem., 1970, 23, 185.

    Article  Google Scholar 

  12. H. W. Post, J. Org. Chem., 1940, 5, 244.

    Article  CAS  Google Scholar 

  13. G. Drehfahl, H. H. Horhold, K. Kuhne, Chem. Ber., 1965, 98, 1826.

    Article  Google Scholar 

  14. K. N. Houk, J. Am. Chem. Soc., 1972, 94, 8953.

    Article  CAS  Google Scholar 

  15. K. N. Houk, A. Bimanand, D. Mukherjee, J. Sims, Y.-M. Chang, D. C. Kaufman, N. L. Domelsmith, Heterocycles, 1977, 7, 293.

    Article  CAS  Google Scholar 

  16. W. J. Bland, R. Davis, J. L. A. Durrant, J. Organomet. Chem., 1982, 234, C20.

    Article  CAS  Google Scholar 

  17. I. V. Bodrikov, I. I. Grinval’d, A. N. Artemov, L. I. Bazhan, I. Yu. Kalagaev, Zh. Obshch. Khim., 2010, 80, 24 [Russ. J. Gen. Chem. (Engl. Transl.), 2010, 80, 20].

    Google Scholar 

  18. Organic solvents; Physical Properties and Methods of Purification, Intersci. Publ. Inc., New York—London, 1955, 552 pp.

  19. Organisch-Chemische Experimentierkunst, 2 Auflage, Johann Ambrosius Barth, Leipzig, 1948, 824 S.

  20. G. M. Sheldrick, SADABS, 1997, Bruker AXS, Inc., Madison (WI), USA.

    Google Scholar 

  21. G. M. Sheldrick, Acta Crystallogr., Sect. A, Found. Crystallogr., 2008, 64, 112.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to N. Yu. Zarovkina.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1382–1387, June, 2013.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Artemov, A.N., Sazonova, E.V. & Zarovkina, N.Y. 1,3-Dipolar cycloaddition reaction of nitrone η6-(arene)chromium tricarbonyl complexes with styrene and η6-(styrene)chromium tricarbonyl. Russ Chem Bull 62, 1382–1387 (2013). https://doi.org/10.1007/s11172-013-0197-8

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-013-0197-8

Key words

Navigation