Block copolymerization of cellulose derivatives with other polymers is a promising approach to impart novel functionality to cellulosic materials. Herein we report a terminal olefination of cellulose triacetate (CTA) for use in the synthesis of polysaccharide-based linear diblock copolymers via olefin cross-metathesis (CM). For preparing the olefin-terminated cellulosic segments, CTA was first subjected to a hydrogen bromide-mediated chain degradation reaction to introduce a single glycosidic Br atom on the reducing end of CTA. The reaction conditions were varied to control the degree of polymerization (DP) and bromination of CTA. Then the terminally brominated CTA was coupled with an ω-unsaturated carboxylic acid or alcohol by classical Koenigs-Knorr reaction. The CTAs having an ω-olefin substituent at the reducing end anomeric position (C-1) were characterized by 1H-NMR and GPC measurements, for use in CM reactions with mono-olefin terminated vinyl polymers.

Terminal olefination of cellulose triacetate for synthesis of cellulosic diblock copolymer via olefin cross-metathesis

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