Skip to main content
SpringerLink
Log in

Hydrophobic acceleration in the Diels—Alder reaction of 9-hydroxymethylanthracene with N-phenylmaleimide

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

Abstract

The Diels—Alder reaction rates of 9-hydroxymethylanthracene with N-phenylmaleimide and N-ethylmaleimide in water, butan-1-ol, ethylene glycol, acetonitrile, chloroform, and 1,4-dioxane have been compared.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. V. D. Kiselev, I. I. Shakirova, A. I. Konovalov, Russ. Chem. Bull. (Int. Ed.), 2013, 62, 285 [Izv. AN, Ser Khim., 2013, 290].

    Article  CAS  Google Scholar 

  2. V. D. Kiselev, A. I. Konovalov, J. Phys. Org. Chem., 2009, 22, 466.

    Article  CAS  Google Scholar 

  3. F. Wurche, F.-G. Klärner, in High Pressure Chemistry, Eds R. van Eldik, F.-G. Klärner, Wiley–VCH, Weinheim, 2002, p. 77.

    Google Scholar 

  4. O. Diels, K. Alder, H. Nienburg, O. Schmalbeck, Liebigs Ann. Chem., 1931, 490, 243.

    Article  Google Scholar 

  5. R. B. Woodward, H. Baer, J. Am. Chem. Soc., 1948, 70, 1161.

    Article  CAS  Google Scholar 

  6. D. C. Rideout, R. Breslow, J. Am. Chem. Soc., 1980, 102, 7816.

    Article  CAS  Google Scholar 

  7. R. Breslow, U. Maitra, D. Rideout, Tetrahedron Lett., 1983, 24, 1901.

    Article  CAS  Google Scholar 

  8. R. Breslow, U. Maitra, Tetrahedron Lett., 1984, 25, 1239.

    Article  CAS  Google Scholar 

  9. R. Breslow, T. Guo, J. Am. Chem. Soc., 1988, 110, 5613.

    Article  CAS  Google Scholar 

  10. J. Light, R. Breslow, Tetrahedron Lett., 1990, 31, 2957.

    Article  CAS  Google Scholar 

  11. R. Breslow, Acc. Chem. Res., 1991, 24, 159.

    Article  CAS  Google Scholar 

  12. W. Blokzijl, M. J. Blandamer, J. B. F. N. Engberts, J. Am. Chem. Soc., 1991, 113, 4241.

    Article  CAS  Google Scholar 

  13. W. Blokzijl, J. B. F. N. Engberts, J. Am. Chem. Soc., 1992, 114, 5440.

    Article  CAS  Google Scholar 

  14. S. Horiuchi, T. Murase, M. Fujita, Chem. Asian J., 2011, 6, 1839.

    Article  CAS  Google Scholar 

  15. C.-J. Li, Chem. Rev., 1993, 93, 2023.

    Article  CAS  Google Scholar 

  16. X. Chen, J. F. Dobson, C. L. Raston, Chem. Commun., 2012, 48, 3703.

    Article  CAS  Google Scholar 

  17. L. Yasmin, K. A. Stubbs, C. L. Raston, Tetrahedron Lett., 2014, 55, 2246.

    Article  CAS  Google Scholar 

  18. N. S. Isaacs, L. Maksimovich, A. Laila, J. Chem. Soc., Perkin Trans. 2, 1994, 495.

    Google Scholar 

  19. M. Sortino, V. C. Filho, R. Correa, S. Zacchino, Bioorg. Med. Chem., 2008, 16, 560.

    Article  CAS  Google Scholar 

  20. V. D. Kiselev, J. G. Miller, J. Am. Chem. Soc., 1975, 97, 4036.

    Article  CAS  Google Scholar 

  21. V. D. Kiselev, Int. J. Chem. Kin., 2013, 45, 613.

    Article  CAS  Google Scholar 

  22. V. D. Kiselev, D. A. Kornilov, I. I. Lekomtseva, A. I. Konovalov, Int. J. Chem. Kin., 2015, 47, 289.

    Article  CAS  Google Scholar 

  23. R. Khan, T. P. Singh, M. D. Singh, Synlett, 2014, 25, 696.

    Article  CAS  Google Scholar 

  24. M. Sortino, V. S. Filho, R. Correa, S. Zacchino, Bioorg. Med. Chem., 2008, 16, 560.

    Article  CAS  Google Scholar 

  25. C.-H. Tung, J.-Q. Guan, J. Org. Chem., 1998, 63, 5857.

    Article  CAS  Google Scholar 

  26. A. Maciejewski, J. Photochem. Photobiol., A, 1990, 51, 87.

    Article  CAS  Google Scholar 

  27. S. Narayan, J. Muldoon, M. G. Finn, V. V. Fokin, H. C. Kolb, K. B. Sharpless, Angew. Chem., Int. Ed., 2005, 44, 3275.

    Article  CAS  Google Scholar 

  28. Y. Jung, R. A. Marcus, J. Am. Chem. Soc., 2007, 129, 5492.

    Article  CAS  Google Scholar 

  29. Y.-J. Zuo, J. Qu, J. Org. Chem., 2014, 79, 6832.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. A. M. Butlerov Institute of Chemistry of Kazan Federal University, 18 ul. Kremlyovskaya, 420008, Kazan, Russian Federation

    V. D. Kiselev, H. A. Kashaeva, L. N. Potapova, D. A. Kornilov & L. I. Latypova

  2. A. E. Arbuzov Institute of Organic and Physical Chemistry of Kazan Scientific Center of Russian Academy of Sciences, 8 ul. Arbuzova, 420008, Kazan, Russian Federation

    A. I. Konovalov

Authors
  1. V. D. Kiselev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. H. A. Kashaeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. L. N. Potapova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. D. A. Kornilov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. L. I. Latypova
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. I. Konovalov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. D. Kiselev.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2202—2205, September, 2016.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kiselev, V.D., Kashaeva, H.A., Potapova, L.N. et al. Hydrophobic acceleration in the Diels—Alder reaction of 9-hydroxymethylanthracene with N-phenylmaleimide. Russ Chem Bull 65, 2202–2205 (2016). https://doi.org/10.1007/s11172-016-1568-8

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-016-1568-8

Key words

Search

Navigation