Polymeric Separation Media. New Functionalized Polymers for the Selective Removal of Haptens from Complex Organic Mixtures

  • Jean M. J. Fréchet
  • Claude Benezra
Part of the Polymer Science and Technology book series (volume 16)


Among the numerous properties of functional polymers, one which has been of interest to us recently is their ability to “fish out”1 selectively one type of functionality from a complex reaction mixture. Our first contribution2 to this field was the development of a polystyryl boronic acid resin which was capable of binding selectively cis-diols. For example, the separation of cis 1,2-cyclohexanediol from its trans isomer could be carried out efficiently by treatment of the commercially available mixture of isomers with the boronic acid resin using either a batch or a column technique2. Boronate formation occurs exclusively with the cis diol which is thus retained by the polymer from which it can be cleaved later by addition of moist solvent or alcohol. This method can also be used with 1,3 or 1,4 diols and is of particular value with carbohydrate derivatives3–4 Other noteworthy applications of functional polymers, in which their ability to extract a component from a complex mixture is used for synthetic purposes, include the preparation of a threaded macrocycle5, the synthesis of an unsymmetrical tetraarylporphyrin6, and the preparation of a dideoxy-sugar of biological importance such as methyl α-D-paratoside1.


Allergic Contact Dermatitis Michael Addition Sesquiterpene Lactone Functional Polymer Antitumour Agent 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    J. M. J. Frechet, Tetrahedron, in press (1980)Google Scholar
  2. 2.
    E. Seymour and J. M. J. Frechet, Tetrahedron Lett., 3669 (1976)Google Scholar
  3. 3.
    J. M. J. Frechet, L. J. Nuyens and E. Seymour, J. Am. Chem. Soc., 101, 432 (1979). E. Seymour and J. M. J. Frechet, Tetrahedron Lett., 1149 (1976)CrossRefGoogle Scholar
  4. 4.
    K. Krohn, K. Eberlein, and G. Gercken, J. Chromatog., 153, 550 (1978)CrossRefGoogle Scholar
  5. 5.
    I. T. Harrison and S. Harrison, J. Am. Chem. Soc., 89, 5723 (1967)CrossRefGoogle Scholar
  6. 6.
    C. C. Leznoff and P. I. Svirskaya, Angew. Chem. Int. Ed., 17, 947 (1978)Google Scholar
  7. 7.
    A. Cheminat, C. Benezra, M. J. Farrall and J. M. J. Frechet, Tetrahedron Lett, 21, 617 (1980)CrossRefGoogle Scholar
  8. 8.
    J. M. J. Frechet, M. J. Farrall, A. Cheminat and C. Benezra, Polym. Prep., 21 (2), 101 (1980).CrossRefGoogle Scholar
  9. 9.
    S. M. Kupchan, Fed. Proc., 33, 2288 (1974) I. H. Hall, K. Lee, C. O. Starnes, S. A. Eigebaly, T. Ibuka, Y. Wu, T. Kimura, and M. Haruna, J. Pharmaceut. Sci., 67, 1235 (1978).Google Scholar
  10. 10.
    Y. R. Naves, Helv. Chim. Acta, 31, 1172 (1948); B. Maurer and A. Grieder, Helv. Chim. Acta, 60, 2177 (1977);CrossRefGoogle Scholar
  11. 11.
    J. C. Mitchell and W. L. Epstein, Arch. Dermatol., 110, 871 (1974)CrossRefGoogle Scholar
  12. 12.
    A. Cheminat, C. Benezra, M. J. Farrall and J. M. J. Frechet, submitted for publication.Google Scholar
  13. 13.
    A. Cheminat, C. Benezra, M. de Smet and J. M. J. Frechet, unpublished results.Google Scholar

Copyright information

© Plenum Press, New York 1982

Authors and Affiliations

  • Jean M. J. Fréchet
    • 1
    • 2
  • Claude Benezra
    • 1
    • 2
  1. 1.Department of ChemistryUniversity of OttawaOttawaCanada
  2. 2.Laboratoire de Dermato-Chimie Clinique DermatologiqueCHR de StrasbourgStrasbourgFrance

Personalised recommendations