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Electrochemical carboxylation of β-cyclodextrin/1-(3-phenoxyphenyl)-1-chloroethane inclusion complex on a glassy-carbon cathode in anhydrous dimethylformamide

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Abstract

Inclusion complexes of β-cyclodextrin with 1-(3-phenoxyphenyl)-1-chloroethane in the “guest-host” molar ratio of 1: 2 are synthesized, isolated, and characterized. It is shown that preparative electrocarboxylation of β-cyclodextrin/1-(3-phenoxyphenyl)-1-chloroethane inclusion complex on a glassy-carbon cathode in dimethylformamide leads to the formation of S-form of 2-(3-phenoxyphenyl)propionic acid (S-Phenoprofen) with an optical yield of ∼20%. In addition to the acid, a dimer of electrochemically generated intermediates forms.

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References

  1. Stepanov, A.A., Grachev, M.K., Kurochkina, G.I., Sipin, V.S., and Grinberg, V.A., Elektrokhimiya, 2007, vol. 43, pp. 1277–1284 [Russ. J. Electrochem. (Engl. Transl.), vol. 43, pp. 1211–1218].

    Google Scholar 

  2. Senboku, H., Kanaya, H., Fujimura, Y., and Tokuda, M., J. Electroanal. Chem., 2001, vol. 507, pp. 82–88.

    Article  CAS  Google Scholar 

  3. Hartman, R., Buchborn, H., and Kranzfelder, G., J. Med. Chem, 1981, pp. 1192–1197.

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

    Article  CAS  Google Scholar 

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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

  3. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninskii pr. 31, Moscow, 119991, Russia

    V. A. Grinberg

Authors
  1. A. A. Stepanov
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  2. M. K. Grachev
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  3. G. I. Kurochkina
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  4. V. A. Grinberg
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Corresponding author

Correspondence to V. A. Grinberg.

Additional information

Original Russian Text © A.A. Stepanov, M.K. Grachev, G.I. Kurochkina, V.A. Grinberg, 2008, published in Elektrokhimiya, 2008, Vol. 44, No. 12, pp. 1498–1503.

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Stepanov, A.A., Grachev, M.K., Kurochkina, G.I. et al. Electrochemical carboxylation of β-cyclodextrin/1-(3-phenoxyphenyl)-1-chloroethane inclusion complex on a glassy-carbon cathode in anhydrous dimethylformamide. Russ J Electrochem 44, 1397–1402 (2008). https://doi.org/10.1134/S1023193508120148

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  • DOI: https://doi.org/10.1134/S1023193508120148

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