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Nucleophilic displacement reactions on tosyl cellulose by chiral amines

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Summary

New 6-deoxy-6-amino cellulose derivatives with a degree of substitution (DS) in the range from 0.4 to 0.6 were synthesized by nucleophilic displacement (SN) reactions of cellulose tosylates (DSTos 0.74 and 1.29) with R(+)-, S(−)- and racemic 1-phenylethylamine under homogeneous conditions in N,N-dimethylformamide and water. The structure of the polymers was characterized by elemental analysis, FTIR and 13C NMR spectroscopy. The DS values obtained as well as the optical rotation and circular dichroism measurements in dimethyl sulfoxide reveal that the initial chirality of the cellulose backbone does not have any significant influence on its reactivity with either of the two enantiomeric amines.

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Authors and Affiliations

  1. Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University of Jena, Humboldtstrasse 10, D-07743 Jena, Germany, , , , , , DE

    Th. Heinze & A. Koschella

  2. Institute of Molecular Biology, Friedrich Schiller University of Jena, Winzerlaer Strasse 10, D-07745 Jena, Germany, , , , , , DE

    L. Magdaleno-Maiza & A. S. Ulrich

Authors
  1. Th. Heinze
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  2. A. Koschella
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  3. L. Magdaleno-Maiza
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  4. A. S. Ulrich
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Received: 21 September 2000/Accepted: 5 January 2001

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Heinze, T., Koschella, A., Magdaleno-Maiza, L. et al. Nucleophilic displacement reactions on tosyl cellulose by chiral amines. Polymer Bulletin 46, 7–13 (2001). https://doi.org/10.1007/s002890170082

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  • DOI: https://doi.org/10.1007/s002890170082

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