Skip to main content
SpringerLink
Log in

Synthesis and electrochemical behavior of inclusion complexes based on β-cyclodextrin and alkylaromatic compounds: Electrochemical carboxylation of the β-cyclodextrin-1-(4-isobutylphenyl)ethylchloride inclusion complex on a glassy-carbon cathode in anhydrous dimethylformamide

  • Published:
Russian Journal of Electrochemistry Aims and scope Submit manuscript

Abstract

Inclusion complexes of β-cyclodextrin with alkylaromatic compounds β-cyclodextrin-1-(4-isobutylphenyl)ethylchloride in the “guest-host” molar ratio of 1 : 2 and β-cyclodextrin-methyl-(4-isobutylphenyl)ketone in the “guest-host” molar ratio of 1 : 1, are synthesized, isolated, and characterized. It is shown that preparative electrocarboxylation of the inclusion complex β-cyclodextrin-1-(4-isobutylphenyl)ethylchloride on a glassy-carbon cathode with a dissolving magnesium anode in dimethylformamide affords S-forms of 2-(4-isobutylphenyl)propionic acid (S-Ibuprofen) in a high enantiomeric excess (97%). In addition to the acid, a dimer and a hydride form from the corresponding intermediates.

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. Stepanov, A.A., Volodin, Yu.Yu., Grachev, M.K., Kurochkina, G.I., Syrtsev, A.N., and Grinberg, V.A., Elektrokhimiya, 2002, vol. 38, p. 1487.

    Google Scholar 

  2. Hayaski, T., Konishi, M., Fukushima, M., Kanehira, K., and Hioh, T., J. Org. Chem., 1983, vol. 48, p. 2195

    Article  Google Scholar 

  3. Cyclodextrins and Their Industrial Uses, Duchêne, de Santé, Eds., 1987; Szejtli, J., Chem. Rev., 1998, vol. 98, p. 1743.

  4. Hedges, A.R., Chem. Rev., 1998, vol. 98, p. 2035.

    Article  CAS  Google Scholar 

  5. Wenz, G., Angew. Chem. Int. Ed. Engl., 1994, vol. 33, p. 803.

    Article  Google Scholar 

  6. Davydova, S.L., Udivitel’nye makrotsikly (The Amazing Macrocycles), Leningrad: Khimiya, 1989.

    Google Scholar 

  7. Hromadova, M., Pospisil, L. Zalis, S., and Fanelli, N., J. Inclusion Phenom. Macrocyclic Chem., 2002, vol. 44, p. 373.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, ul. Vavilova 28, Moscow, 117812, Russia

    A. A. Stepanov

  2. Moscow State Pedagogical University, ul. Malaya Pirogovskaya 1, Moscow, 115409, Russia

    M. K. Grachev, G. I. Kurochkina & S. V. Sipin

  3. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninskii pr. 31, Moscow, 119071, Russia

    V. A. Grinberg

Authors
  1. A. A. Stepanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. K. Grachev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. I. Kurochkina
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S. V. Sipin
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. V. A. Grinberg
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Original Russian Text © A.A. Stepanov, M.K. Grachev, G.I. Kurochkina, S.V. Sipin, V.A. Grinberg, 2007, published in Elektrokhimiya, 2007, Vol. 43, No. 10, pp. 1277–1284.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Stepanov, A.A., Grachev, M.K., Kurochkina, G.I. et al. Synthesis and electrochemical behavior of inclusion complexes based on β-cyclodextrin and alkylaromatic compounds: Electrochemical carboxylation of the β-cyclodextrin-1-(4-isobutylphenyl)ethylchloride inclusion complex on a glassy-carbon cathode in anhydrous dimethylformamide. Russ J Electrochem 43, 1211–1218 (2007). https://doi.org/10.1134/S1023193507100175

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1023193507100175

Key words

Search

Navigation