New Poly(oxyethylene) Derivatives from Diels-Alder Reactions of 3-[Methoxypoly(oxyethylene)]methylene Furan
Abstract
A new poly(ethylene glycol) derivative, 3‐[methoxypoly(oxyethylene)]methylene furan, I, was prepared from the reaction of 3‐furanmethanol with the mesylate of methoxypoly(oxyethylene) in tetrahydrofuran. The degree of end‐group conversion, as determined by NMR spectroscopy, was 100%. The Diels-Alder reactions of I with N‐phenylmaleimide, N‐glycinylmaleimide, maleic anhydride, N,N'‐hexamethylene bismaleimide, and diethyl acetylenedicarboxylate resulted in the corresponding adducts. For the adduct derived from I and N‐phenylmaleimide, its thermal reversible character was confirmed by applying a retro‐Diels-Alder reaction in the presence of a large excess of 2‐methylfuran, which restored the initial polymer I quantitatively. The adduct obtained from I and N‐glycinylmaleimide was converted into its succinimidyl ester and its hydrolysis rate in phosphate buffer (pH = 8) was determined. The reactivity of the adduct derived from I and N,N'‐hexamethylene bismaleimide with benzyl mercaptan was also investigated.
Department(s)
Chemistry and Biochemistry
Document Type
Article
DOI
https://doi.org/10.1002/macp.200500232
Keywords
biocompatibility, diels‐alder reaction, hydrophilic polymers, polyethers, poly(ethylene glycol)
Publication Date
2005
Recommended Citation
Sedaghat‐Herati, Reza, Almary Chacon, Mary E. Hansen, and Skander Yalaoui. "New Poly (oxyethylene) Derivatives from Diels–Alder Reactions of 3‐[Methoxypoly (oxyethylene)] methylene Furan." Macromolecular Chemistry and Physics 206, no. 19 (2005): 1981-1987.
Journal Title
Macromolecular Chemistry and Physics
