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Phase-Transfer Catalysis in Alkaline Hydrolysis of N-Benzyloxycarbonylglycine 4-Nitrophenyl Ester in the Two-Phase System Chloroform-Borate Buffer

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Abstract

Alkaline hydrolysis of N-benzyloxycarbonylglycine 4-nitrophenyl ester in the two-phase system chloroform-borate buffer (pH 10 and 11) in the presence of C16H33NMe3Br and Ph4PZ (Z = Cl, Br, I) at 25°C follows the extraction mechanism where the rate-determining stage is the chemical reaction in the organic phase. The different kinetic profiles of the reaction depending on the nature of Z- were explained in terms of concurrent extraction of three kinds of anions: nucleophile OH-, nucleofuge 4-NO2C6H4O-, and foreign ion Z-.

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Authors and Affiliations

  1. Donetsk State University, ul. Universitetskaya 24, Donetsk, 383050, Ukraine

    O. V. Baranova, V. V. Kosmynin & A. N. Shendrik

  2. Ukrainian National Academy of Sciences, Litvinenko Institute of Physical Organic and Coal Chemistry, Ukraine

    V. A. Savelova, A. F. Popov & B. V. Panchenko

Authors
  1. O. V. Baranova
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  2. V. V. Kosmynin
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  3. V. A. Savelova
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  4. A. F. Popov
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  5. B. V. Panchenko
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  6. A. N. Shendrik
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Baranova, O.V., Kosmynin, V.V., Savelova, V.A. et al. Phase-Transfer Catalysis in Alkaline Hydrolysis of N-Benzyloxycarbonylglycine 4-Nitrophenyl Ester in the Two-Phase System Chloroform-Borate Buffer. Russian Journal of Organic Chemistry 37, 667–672 (2001). https://doi.org/10.1023/A:1012439531879

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  • DOI: https://doi.org/10.1023/A:1012439531879

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