New Poly(oxyethylene) Derivatives from Diels-Alder Reactions of 3-[Methoxypoly(oxyethylene)]methylene Furan


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.


Chemistry and Biochemistry

Document Type




biocompatibility, diels‐alder reaction, hydrophilic polymers, polyethers, poly(ethylene glycol)

Publication Date


Journal Title

Macromolecular Chemistry and Physics