Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
7787546 | Carbohydrate Polymers | 2015 | 8 Pages |
Abstract
We describe the first synthesis of hydroxy-functionalized polysaccharide esters via chemoselective olefin hydroboration-oxidation in the presence of ester groups. Cellulose esters with terminally olefinic side chains were first synthesized by esterification of commercially available cellulose esters (e.g., cellulose acetate) with undec-10-enoyl chloride or pent-4-enoyl chloride. Subsequent two-step, one-pot hydroboration-oxidation reactions of the cellulose esters were performed, using 9-borabicyclo[3.3.1]nonane as hydroboration agent, followed by oxidizing the intermediate borane to a hydroxyl group using mildly alkaline H2O2. Sodium acetate was used as a weak base to catalyze the oxidation, thereby minimizing undesired ester hydrolysis. Characterization methods including FTIR, 1H, and 13C NMR proved the selectivity of the hydroboration-oxidation pathway, providing a family of novel cellulose Ï-hydroxyalkanoyl esters that were previously difficult to access.
Related Topics
Physical Sciences and Engineering
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Authors
Xiangtao Meng, Emily A. York, Shu Liu, Kevin J. Edgar,