Skip to main content
SpringerLink
Log in

Stereo/regio-controlled cyclization of polychlorohex-5-enoic acids into substituted cyclobutanes

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

Abstract

A new method of synthesis was developed for functionally substituted cyclobutanecarboxylic acids based on an intramolecular cyclization of derivatives of the 2,2,4,6,6-pentachloro-3,3-dimethylhex-5-enoic acid in the presence of the copper(I) amine complexes. The cyclization proceeds both regiospecifically and stereoselectively, and the stereoisomeric composition of the products depends on the capability of the functional group in the initial polychloroalkenoic acid to coordinate to the transition metal ion. A reaction mechanism is suggested explaining the region/stereo-controlled course of the cyclization process.

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. Freidlina, R.Kh., Velichko, F.K., Zlotskii, S.S., Rakhmankulov, D.L., and Terent’ev, A.B., Radikal’naya telomerizatsiya (Radical Telomerization), Moscow: Khimiya, 1988, 288 p.

    Google Scholar 

  2. Iqbal, J., Bhatia, B., Nayyar, N.K. Chem. Rev., 1994, vol. 94, p. 519; Forti, L., Ghelfi, F., and Pagnoni, U.M., Tetrahedron Lett., 1996, and 37, p. 2077.

    Article  CAS  Google Scholar 

  3. Nagashima, H., Seki, K., Ozaki, N., Wakamatsu, H., Itoh, K., Tomo, Y., and Tsuji, J. J. Org. Chem., 1990, vol. 55, p. 985; Pirrung, F.O.H., Hiemstra, H., and Speckamp, W.N., Tehnhedron, 1994, and 50, 12415; Cassayre, J., Quiclet-Sire, B., Saunier, J.-B., and Zard, S.Z., Tetrahedron, 1998, and 54, p. 1029; Ghelfi, F., Bellesia, F., Forti, L., Ghirardini, G., Grandi, R., Liberfini, E., Montemaggi, M.C., Pagnoni, U.M., Pinetti, A., De, Buyck, L., and Parsons, A.F., Tetrahedron, 1999, vol. 55, p. 5839; Nagashima, H., Isono, Y., and Iwamatsu, Sh., J. Org. Chem., 2001, vol. 66, p. 315.

    Article  CAS  Google Scholar 

  4. Hayes, T.K., Freyer, A.J., Parvez, M., and Weinreb, S.M., J. Org. Chem., 1986, vol. 51, p. 5501; Garri, M.L., Parvez, M., and Weinreb, S.M., Tetrahedron, 1988, vol. 44, p. 4671; Thomas, K.H., Villani, R., and Weinreb, S.M., J. Am. Chem. Soc., 1988, vol. 110, p. 5533; Phelps, J.C., Bergreiter, D.E., Lee, G.M., Villani, R., and Weinreb, S.M., Tetrahedron Lett., 1989, vol. 30, p. 3915; Garri, M.L. and Weinreb, S.M., J. Org. Chem., 1990, vol. 55, p. 1281.

    Article  CAS  Google Scholar 

  5. Clark, A.J., Chem. Soc. Rev., 2002, vol. 31, p. 1.

    Article  CAS  Google Scholar 

  6. Lee-Ruff, E. and Mladenova, G., Chem. Rev., 2003, vol. 103, p. 1449; Namyslo, J.C. and Kaufmann, D.E., Chem. Rev., 2003, vol. 103, p. 1485.

    Article  CAS  Google Scholar 

  7. Ichikawa, M., Takahashi, M., Aoyagi, S., and Kibayashi, C., J. Am. Chem. Soc., 2004, vol. 126, p. 16553; Avenoza, A., Busto, J.H., Canal, N., and Peregrina, J.M., J. Org. Chem., 2005, vol. 70, p. 330; Taber, D.F. and Frankowski, K.J., J. Org. Chem., 2005, vol. 70, p. 6417; Hazelard, D., Fadel, A., and Girard, C., Tetrahedron: Asymmetry, 2006, vol. 17, p. 1457.

    Article  CAS  Google Scholar 

  8. Clark, A.J., Filik, R.P., Haddleton, D.M., Radigue, A., Sanders, C.J., Thomas, G.H., and Smith, M.E., J. Org. Chem., 1999, vol. 64, p. 8954; De Campo, F., Lastécouéres, D., and Verlhac, J.-B., J. Chem. Soc., Perkin, Trans. 1, 2000, p. 575; Kamigaito, M., Ando, T., and Sawamoto, M. Chem. Rev., 2001, vol. 101, p. 3689.

    Article  CAS  Google Scholar 

  9. Quebatte, L., Scopelliti, R., and Severin, K., Angew. Chem., Int. Ed., 2004, vol. 43, p. 1520; Thommes, K., Icli, B., Scopelliti, R., and Severin, K., Chem. Eur. J., 2007, vol. 13, p. 6899; Wolf, J., Thommes, K., Briel, O., Scopelliti, R., and Severin, K. Organometallics, 2008, vol. 27, p. 4464.

    Article  CAS  Google Scholar 

  10. Stepanyan, A.N., Mikaelyan, A.R., Ovivyan, E.M., and Badanyan, Sh.O., Arm. Khim. Zh., 1992, vol. 45, p. 243.

    Google Scholar 

  11. Zubritskii, L.M., Startsev, V.V., and Petrov, A.A., Zh. Org. Khim., 1994, vol. 30, p. 181.

    CAS  Google Scholar 

  12. Badanyan, Sh.O., Stepanyan, A.N., Mikaelyan, A.R., Ovivyan, E.M., and Panosyan, G.A., Zh. Org. Khim., 1997, vol. 33, p. 44.

    Google Scholar 

  13. Terzyan, S.S., Mikaelyan, A.R., and Badanyan, Sh.O., Zh. Strukt. Khim., 1998, vol. 39, p. 172; Karapetyan, A.A., Mikaelyan, A.R., Grigoryan, A.M., and Badanyan, Sh.O., Zh. Strukt. Khim., 2000, vol. 41, p. 201.

    Google Scholar 

  14. Vogeli, U., Herz, D. and Von Philipsborn, W., Org. Magn. Res., 1980, vol. 13, p. 200; Sergeev, N.M., Chertkov, V.A., Torocheshnikov, V.N., Rosnyatovsky, V.A., Panosyan, G.A., Shakhatuni, A.G., and Khrimian, A.P., Magn. Res. Chem., 1991, vol. 29, p. 762.

    Article  Google Scholar 

  15. Polyakova, A.A. and Khmel’nitskii, R.A., Mass-spektrometriya v organicheskoi khimii (Mass-Spectrometry in Organic Chemistry), Leningrad: Khimiya, 1972, p. 155.

    Google Scholar 

  16. Matyjaszewski, K. and Xia, J., Chem. Rev., 2001, vol. 101, p. 2921; Poli, R., Angew. Chem., Int. Ed., 2006, vol. 45, p. 5058.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Armenian State Engineering University (Polytechnic), Yerevan, 000, Armenia

    A. R. Mikaelyan

Authors
  1. A. R. Mikaelyan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. R. Mikaelyan.

Additional information

Original Russian Text © A.R. Mikaelyan, 2010, published in Zhurnal Organicheskoi Khimii, 2010, Vol. 46, No. 11, pp. 1655–1659.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Mikaelyan, A.R. Stereo/regio-controlled cyclization of polychlorohex-5-enoic acids into substituted cyclobutanes. Russ J Org Chem 46, 1662–1666 (2010). https://doi.org/10.1134/S1070428010110084

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428010110084

Keywords

Search

Navigation