Skip to main content
SpringerLink
Log in

Isomerization of dimethylenecyclopropanes in benzofulvenes in the presence of Lewis acids

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

1,1-Diaryl-2-(1-methylethylidene)-3-methylenecyclopropanes in the presence of Lewis acid isomerize in benzofulvene derivatives.

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. Aburano, D., Inagaki, F., Tomonaga, S., and Mukai, C., J. Org. Chem., 2009, vol. 74, p. 5590.

    Article  CAS  Google Scholar 

  2. Clegg, N.J., Paruthiyil, S., Leitman, D.C., and Scanlan, T.S., J. Med. Chem., 2005, vol. 48, p. 5989.

    Article  CAS  Google Scholar 

  3. Gao, H., Katzenellenbogen, J.A., Garg, R., and Hansch, C., Chem. Rev., 1999, vol. 99, p. 723.

    Article  CAS  Google Scholar 

  4. Görl, C. and Alt, H.G., J. Organometal. Chem., 2007, vol. 692, p. 5727.

    Article  Google Scholar 

  5. Gaede, P.E., J. Organometal. Chem., 2000, vol. 616, p. 29.

    Article  Google Scholar 

  6. Rogers, J.S., Lachicotte, R.J., and Bazan, G.C., Organometallics, 1999, vol. 18, p. 3976.

    Article  CAS  Google Scholar 

  7. Cappelli, A., Galeazzi, S., Giuliani, G., Anzini, M., Donati, A., Zetta, L., Mendichi, R., Aggravi, M., Giorgi, G., Paccagnini, E., and Vomero, S., Macromolecules, 2007, vol. 40, p. 3005.

    Article  CAS  Google Scholar 

  8. Nakano, T., Yade, T., Fukuda, Y., Yamaguchi, T., and Okumura, S., Macromolecules, 2005, vol. 38, p. 8140.

    Article  CAS  Google Scholar 

  9. Cappelli, A., Grisci, G., Paolino, M., Castriconi, F., Giuliani, G., Donati, A., Lamponi, S., Mendichi, R., Boccia, A.C., Samperi, F., Battiato, S., Paccagnini, E., Gentile, M., Licciardi, M., Giammona, G., and Vomero, S., Chem. Eur. J., 2013, vol. 19, p. 9710.

    Article  CAS  Google Scholar 

  10. Londergan, T.M., Teng, C.J., and Weber, W.P., Macromolecules, 1999, vol. 32, p. 1111.

    Article  CAS  Google Scholar 

  11. Cappelli, A., Pericot Mohr, G., Anzini, M., Vomero, S., Donati, A., Casolaro, M., Mendichi, R., Giorgi, G., and Makovec, F., J. Org. Chem., 2003, vol. 68, p. 9473.

    Article  CAS  Google Scholar 

  12. Jeffrey, J.L. and Sarpong, R., Tetrahedron Lett., 2009, vol. 50, p. 1969.

    Article  CAS  Google Scholar 

  13. Alcalde, E., Mesquida, N., Frigola, J., Loìpez-Peìrez, S., and Merce, R., Org. Biomol. Chem., 2008, vol. 6, p. 3795.

    Article  CAS  Google Scholar 

  14. Reggio, P.H., Basu-Dutt, S., Barnett-Norris, J., Castro, M.T., Hurst, D.P., Seltzman, H.H., Roche, M.J., Gilliam, A.F., Thomas, B.F., Stevenson, L.A., Pertwee, R.G., and Abood, M.E., J. Med. Chem., 1998, vol. 41, p. 5177.

    Article  CAS  Google Scholar 

  15. Walters, M.J., Blobaum, A.L., Kingsley, P.J., Felts, A.S., Sulikowski, G.A., and Marnett, L., J. Bioorg. Med. Chem. Lett., 2009, vol. 19, p. 3271.

    Article  CAS  Google Scholar 

  16. Felts, A.S., Siegel, B.S., Young, S.M., Moth, C.W., Lybrand, T.P., Dannenberg, A.J., Marnett, L.J., and Subbaramaiah, K., J. Med. Chem., 2008, vol. 51, p. 4911.

    Article  CAS  Google Scholar 

  17. Shimizu, S., Shirakawa, S., Suzuki, T., and Sasaki, Y., Tetrahedron, 2001, vol. 57, p. 6169.

    Article  CAS  Google Scholar 

  18. Fringuelli, F., Pani, G., Piermatti, O., and Pizzo, F., Tetrahedron, 1994, vol. 50, p. 11499.

    Article  CAS  Google Scholar 

  19. Zheng, M., Wang, L., Shao, J., and Zhong, Q., Synth. Commun., 1997, vol. 27, p. 1751.

    Article  CAS  Google Scholar 

  20. Lu, W., Zhu, Q., and Yan, C.-G., Synth. Commun., 1997, vol. 27, p. 3985.

    Article  CAS  Google Scholar 

  21. Galin, F.Z., Ignatyuk, V.K., Lakeev, S.N., Rakhimov, R.G., Sultanova, V.S., and Tolstikov, G.A., Russ. J. Org. Chem., 1989, vol. 25, p. 102.

    Google Scholar 

  22. Moeller, A.C., Blom, R., Heyn, R.H., Swang, O., Goerbitz, C.-H., and Seraidaris, T., Eur. J. Inorg. Chem., 2005, p. 1759.

    Google Scholar 

  23. Vavilala, C., Byrne, N., Kraml, C.M., Ho, D.M., and Pascal, R.A. Jr., J. Am. Chem. Soc., 2008, vol. 130, p. 13549.

    Article  CAS  Google Scholar 

  24. Peabody, S.W., Breiner, B., Kovalenko, S.V., Patil, S., and Alabugin, I.V., Org. Biomol. Chem., 2005, vol. 3, p. 218.

    Article  CAS  Google Scholar 

  25. Kovalenko, S.V., Peabody, S., Manoharan, M., Clark, R.J., and Alabugin, I.V., Org. Lett., 2004, vol. 6, p. 2457.

    Article  CAS  Google Scholar 

  26. König, B., Pitsch, W., Klein, M., Vasold, R., Prall, M., and Schreiner, P.R., J. Org. Chem., 2001, vol. 66, p. 1742.

    Article  Google Scholar 

  27. Schmittel, M., Mahajan, A.A., Bucher, G., and Bats, J.W., J. Org. Chem., 2007, vol. 72, p. 2166.

    Article  CAS  Google Scholar 

  28. Schmittel, M. and Vavilala, C., J. Org. Chem., 2005, vol. 70, p. 4865.

    Article  CAS  Google Scholar 

  29. Engels, B., Lennartz, C., Hanrath, M., Schmittel, M., and Strittmatter, M., Angew. Chem., Int. Ed., 1998, vol. 37, p. 1960.

    Article  CAS  Google Scholar 

  30. Bucher, G., Mahajan, A.A., and Schmittel, M., J. Org. Chem., 2008, vol. 73, p. 8815.

    Article  CAS  Google Scholar 

  31. Schmittel, M., Mahajan, A.A., and Bucher, G., J. Am. Chem. Soc., 2005, vol. 127, p. 5324.

    Article  CAS  Google Scholar 

  32. Cordier, P., Aubert, C., Malacria, M., Lacôte, E., and Gandon, V., Angew. Chem., Int. Ed., 2009, vol. 48, p. 8757.

    Article  CAS  Google Scholar 

  33. Lu, B.-L. and Shi, M., Eur. J. Org. Chem., 2011, p. 243.

    Google Scholar 

  34. Chinnagolla, R.K. and Jeganmohan, M., Eur. J. Org. Chem., 2012, p. 417.

    Google Scholar 

  35. Tsuchikama, K., Kasagawa, M., Endo, K., and Shibata, T., Synlett., 2010, p. 97.

    Google Scholar 

  36. Huang, X. and Yewei, Y., Org. Lett., 2007, vol. 9, p. 1667.

    Article  CAS  Google Scholar 

  37. Stepakov, A.V., Larina, A.G., Boitsov, V.M., Molchanov, A.P., Gurzhiy, V.V., and Starova, G.L., Tetrahedron Lett., 2012, vol. 53, p. 3411.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. St. Petersburg State University, Universitetskii pr. 26, St. Petersburg, 198504, Russia

    A. V. Stepakov, A. G. Larina & A. P. Molchanov

Authors
  1. A. V. Stepakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. G. Larina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. P. Molchanov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. V. Stepakov.

Additional information

Original Russian Text © A.V. Stepakov, A.G. Larina, A.P. Molchanov, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 2, pp. 222–225.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Stepakov, A.V., Larina, A.G. & Molchanov, A.P. Isomerization of dimethylenecyclopropanes in benzofulvenes in the presence of Lewis acids. Russ J Org Chem 51, 210–213 (2015). https://doi.org/10.1134/S1070428015020128

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428015020128

Keywords

Search

Navigation