Structural determination of a new carbohydrate-phenolic based resin coupled with urea Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/0z709164z

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  • A resin was synthesized by reacting glucose with urea and phenol under acidic conditions. To better understand the structure of this polymer and the mechanism of its formation, this study was undertaken. It was observed that although the polymer backbone is comprised of a carbohydrate, glucose is not incorporated in this resin in its unaltered state. By isolating key intermediate products, it was hypothesized that glucose reacts with urea to form an imine which deoxygenates to form a keto-imine moeity. The latter can then undergo degradation to form 2-deoxy-D-ribonopyranolactone. The structure of this lactone was established by one and two dimensional proton as well as carbon NMR spectroscopy. Two dimensional heteronuclear correlation and depth experiments also supported this structure as well as the positive-FAB mass spectroscopy. This lactone, or the imine itself, can then undergo homopolymerization as well as heteropolymerization with phenol to form the polymer of this study.
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