Vinyl ether end‐groups in poly(ethylene glycol)s from the Na2CO3‐promoted degradation of 1,3‐dioxolan‐2‐one polymers |
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Authors: | James J. Harrison Anatoli Onopchenko Michael T. Cheng Carrie Y. Chan |
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Abstract: | The Na2CO3‐promoted polymerization of 1,3‐dioxolan‐2‐one (I) to afford poly(ethylene glycol) III was reinvestigated. The reaction appeared to involve a nucleophilic attack against the carbonyl and methylene groups of I to afford poly(carbonate) II with poly(ethylene glycol) linkages and ethylene oxide IV as a side product (10–22%). As the reaction progressed, poly(carbonate) II decreased and poly(ethylene glycol) III increased. Under some conditions, poly(ethylene glycol)s V and VI with vinyl ether terminal groups were formed unexpectedly. The formation of unsaturated products during the polymerization of I/EO (ethylene oxide) has not been reported in the literature. We believe that vinyl ethers were formed from the degradation of poly(carbonate)s and were accompanied by a reduction in molecular weight. The structures of vinyl ethers V and VI were confirmed by hydrogenation of the double bond into the ethyl ether group in VII and VIII, respectively. © 2000 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 38: 152–160, 2000 |
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Keywords: | 1,3‐dioxolan‐2‐one polymerization vinyl ethers sodium carbonate poly(ethylene glycol) mechanism ESI‐MS |
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