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

✍ Scribed by Reza Sedaghat-Herati; Almary Chacon; Mary E. Hansen; Skander Yalaoui

• Book ID: 102487016
• Publisher: John Wiley and Sons
• Year: 2005
• Tongue: English
• Weight: 115 KB
• Volume: 206
• Category: Article
• ISSN: 1022-1352
• DOI: 10.1002/macp.200500232

✦ Synopsis

Abstract

Summary: 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.
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