Nucleophilic displacement reactions on tosyl cellulose by chiral amines

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 displacemen t (SN) reactions of cellulose tosylates (DSTos 0.74 and 1.29) with R(+)-, S (-)- and racemic I-phenylethylamine under homogeneous conditions in N,N-dim ethylformamide and water. The structure of the polymers was characterized b y elemental analysis, FTIR and C-13 NMR spectroscopy. The DS values obtaine d as well as the optical rotation and circular dichroism measurements in di methyl sulfoxide reveal that the initial chirality of the cellulose backbon e does not have any significant influence on its reactivity with either of the two enantiomeric amines.