Poly‐2‐vinylfuran, synthesis, characterization, and diels‐alder reaction with maleic anhydride

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Abstract
Poly‐2‐vinylfuran, synthesized by free‐radical polymerization of 2‐vinylfuran, was characterized by nuclear magnetic resonance (NMR) and infrared (IR) spectroscopy. The pendant furan rings on the polymer backbone were then used as the diene component of a Diels‐Alder reaction with maleic anhydride. The juxtaposition of the furan rings at first suggested an “avalanche” Diels‐Alder reaction, in which the product of one cyclization would be the reactant of the next. A lack of polymer stereoregularity and the reversibility of the Diels‐Alder reaction, however, prevented its formation. On the other hand, when the dienophile was used in a 1:1 molar ratio with respect to furan the smooth reaction produced a new polymer, the maleic anhydride adduct of poly‐2‐vinylfuran, which characterized by NMR and IR spectroscopy, was air stable and soluble in a number of solvents up to 70% transformation. When heated to 160°C the polymer reverted to maleic anhydride and somewhat decomposed poly‐2‐vinylfuran.

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