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Electrochemical reduction of mucochloric acid and its 5-alkoxy derivatives

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Abstract

5-Alkoxy-3-chloro-2(5H)-furanones were synthesized by the electrochemical reduction of 5-alkoxy derivatives of mucochloric acid in acetonitrile on the lead electrode in the presence of acetic acid as a proton donor. A combined analysis of the experimental data and quantum chemical calculation of intermediates indicates the EE D C mechanism of reduction, including the tandem transfer of two electrons with chloride ion elimination at the stage of transfer of the second electron and protonation.

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References

  1. Y. S. Rao, Chem. Rev., 1976, 76, 625.

    Article  CAS  Google Scholar 

  2. A. A. Avetisyan, M. T. Dangyan, Usp. Khim., 1977, 46, 1250 [Russ. Chem. Rev. (Engl. Transl.), 1977, 46].

    Article  CAS  Google Scholar 

  3. D. W. Knight, Contemp. Org. Synth., 1994, 1, 287.

    Article  CAS  Google Scholar 

  4. F. Bellina, R. Rossi, Curr. Org. Chem., 2004, 8, 1089.

    Article  CAS  Google Scholar 

  5. A. R. Kurbangalieva, N. F. Devyatova, A. V. Bogdanov, E. A. Berdnikov, T. G. Mannafov, D. B. Krivolapov, I. A Litvinov, G. A. Chmutova, Phosphorus, Sulfur, Silicon, Relat. Elem., 2007, 182, 607.

    Article  CAS  Google Scholar 

  6. N. F. Devyatova, L. S. Kosolapova, A. R. Kurbangalieva, E. A. Berdnikov, O. A. Lodochnikova, I. A. Litvinov, G. A. Chmutova, Zh. Org. Khim., 2008, 44, 1237 [Russ. J. Org. Chem. (Engl. Transl.), 2008, 44, 1225].

    Google Scholar 

  7. A. R. Kurbangalieva, N. F. Devyatova, L. S. Kosolapova, O. A. Lodochnikova, E. A. Berdnikov, I. A. Litvinov, G. A. Chmutova, Izv. Akad. Nauk, Ser. Khim., 2009, 126 [Russ. Chem. Bull., Int. Ed., 2009, 58, 126].

    Google Scholar 

  8. A. R. Kurbangalieva, O. A. Lodochnikova, N. F. Devyatova, E. A. Berdnikov, O. I. Gnezdilov, I. A. Litvinov, G. A. Chmutova, Tetrahedron, 2010, 66, 9945.

    Article  CAS  Google Scholar 

  9. F. Farina, M. R. Martin, M. V. Martin, S. Ramirez, Afinidad, 1978, 35, 119.

    CAS  Google Scholar 

  10. F. Farina, M. R. Martin, M. V. Martin, Anales de Quimica, 1979, 75, 144.

    CAS  Google Scholar 

  11. N. F. Devyatova, A. R. Kurbangalieva, V. V. Yanilkin, G. A. Chmutova, Izv. Akad. Nauk, Ser. Khim., 2009, 889 [Russ. Chem. Bull., Int. Ed., 2009, 58, 908].

    Google Scholar 

  12. Ch. K. Mann, K. K. Barnes, Electrochemical Reactions in Nonaqueous Systems, Marcel Dekker, Inc., New York, 1970, 560 pp.

    Google Scholar 

  13. A. Weissberger, E. S. Proskauer, J. A. Riddic, E. E. Toops, Organic Solvents. Physical Properties and Methods of Purifications, Interscience Publishers, Inc., New York-London, 1955.

    Google Scholar 

  14. O. N. Vlasov, B. N. Rybakov, L. M. Kogan, Zh. Prikl. Khim., 1968, 41, 373 [J. Appl. Chem. (Engl. Transl.), 1968, 41].

    CAS  Google Scholar 

  15. D. T. Mowry, J. Am. Chem. Soc., 1950, 72, 2535.

    Article  CAS  Google Scholar 

  16. P. L. Fishbein, H. W. Moore, Synth. Commun., 1989, 19, 3283.

    Article  CAS  Google Scholar 

  17. W. Gumulka, J. Kokosinski, Pol. Organika, 1976, 45.

  18. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople, GAUSSIAN 98, Revision A.7, Gaussian, Inc., Pittsburgh (PA), USA, 1998.

    Google Scholar 

  19. F. A. Beland, S. O. Farwell, P. R. Gallis, J. Electroanal. Chem., 1977, 78, 145.

    Article  CAS  Google Scholar 

  20. C. P. Andrieux, A. Merz, J.-M. Saveant, J. Am. Chem. Soc., 1985, 107, 6097.

    Article  CAS  Google Scholar 

  21. V. V. Yanilkin, E. A. Berdnikov, B. I. Buzykin, Elektrokhimiya, 2000, 36, 144 [Russ. J. Electrochem. (Engl. Transl.), 2000, 36, 128].

    Google Scholar 

  22. M. R. Rifi, Electrochemical Reduction of Organic Halides, in Organic Electrochemistry, Ed. M. M. Baizer, M. Dekker Inc., New York, 1973.

    Google Scholar 

  23. E. A. Berdnikov, S. B. Fedorov, Yu. M. Kargin, Zh. Obshch. Khim., 1978, 48, 875 [J. Gen. Chem. USSR (Engl. Transl.), 1978, 48].

    CAS  Google Scholar 

  24. G. A. Chmutova, A. R. Kurbangalieva, A. N. Vedernikov, Zh. Obshch. Khim., 2001, 71, 833 [Russ. J. Gen. Chem. (Engl. Transl.), 2001, 71, 780].

    Google Scholar 

  25. G. A. Chmutova, E. R. Ismagilova, T. I. Madzhidov, Zh. Obshch. Khim., 2009, 79, 1562 [Russ. J. Gen. Chem. (Engl. Transl.), 2009, 79, 1919].

    Google Scholar 

  26. Yu. Yu. Lur’e, Spravochnik po analiticheskoi khimii [Manual on Analytical Chemistry], Khimiya, Moscow, 1989, 448 pp. (in Russian).

  27. R. T. LaLonde, S. Xie, Chem. Res. Tox., 1992, 5, 618.

    Article  CAS  Google Scholar 

  28. Z. Galus, Teoretyczne Podstawy Elektroanalizy Chemicznej, Panstwowe Wydawnictwo Naukowe, Warszawa, 1971.

    Google Scholar 

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Authors and Affiliations

  1. A. M. Butlerov Chemical Institute of the Kazan Federal University, 18 ul. Kremlevskaya, 420008, Kazan, Russian Federation

    L. Z. Latypova, A. R. Kurbangalieva, E. A. Berdnikov & G. A. Chmutova

  2. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 8 ul. Akad. Arbuzova, 420088, Kazan, Russian Federation

    V. V. Yanilkin

Authors
  1. L. Z. Latypova
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  2. V. V. Yanilkin
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  3. A. R. Kurbangalieva
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  4. E. A. Berdnikov
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  5. G. A. Chmutova
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Corresponding author

Correspondence to A. R. Kurbangalieva.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 566–579, March, 2012.

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Latypova, L.Z., Yanilkin, V.V., Kurbangalieva, A.R. et al. Electrochemical reduction of mucochloric acid and its 5-alkoxy derivatives. Russ Chem Bull 61, 568–581 (2012). https://doi.org/10.1007/s11172-012-0083-9

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  • DOI: https://doi.org/10.1007/s11172-012-0083-9

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