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J. Borycki, M. Wilczek, A. Yu. Kolendo

New optically active poly(esterimides) and poly(amideimides).

Part I. Synthesis of optically active monomers

Polimery 2006, No 4, 257


DOI: dx.doi.org/10.14314/polimery.2006.257

Summary

Several diacids, containing imide groups (dicarboxyimides), have been prepared in the reaction of trimellitic anhydride or dianhydrides: pyromellitic, bicyclo[2,2,2]-oct-7-en-2,3,5,6-tetracarboxylic, benzophenone-3,3',4,4'-tetracarboxylic, perylene-3,4,9,10-tetracarboxylic or biphthalic one with optically active α-amino acids such as L-alanine, D-alanine, D/L-alanine, L-leucine, L-isoleucine, L-phenylalanine, L-valine or L-2-aminobutyric acid (Table 1, Scheme A). The products of desired purity were obtained in only few cases (agreement of melting point with literature data, chemical structure confirmed by IR and 1H NMR methods, Fig. 1-4). In majority of reactions the impured products, difficult to separation and identification, were obtained. From the chosen diacids the proper chlorides were obtained via standard reaction with thionyl chloride (Table 2).


Key words: α-amino acids, anhydrides, diacids with imide bonds, synthesis, optical activity


J. Borycki, M. Wilczek, A. Yu. Kolendo

New optically active poly(esterimides) and poly(amideimides). Part I. Synthesis of optically active monomers