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Synthesis and cationic ring-opening polymerization of 2-methylene-7-oxabicyclo[2.2.1]heptane

✍ Scribed by Ruke Bai; Shihua Li; Yinfang Zou; Caiyuan Pan; Toshiyuki Uryu

Publisher
John Wiley and Sons
Year
1994
Tongue
English
Weight
355 KB
Volume
195
Category
Article
ISSN
1022-1352

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✦ Synopsis

Abstract

A new unsaturated bicyclic ether, 2‐methylene‐7‐oxabicyclo[2.2.1]heptane (4) was synthesized by successive Diels‐Alder addition of furan to acrylonitrile, hydrogenation of cyano compound 5, and Hofmann degradation of the quaternary ammonium hydrate 7 derived from the amine 6. Cationic polymerization of the monomer 4 was carried out in CH~2~Cl~2~ using BF~3~ · OEt~2~, PF~5~, SbCl~5~ and SnCl~4~ as catalysts in the temperature range of −20 to −25°C. White or slightly yellow powdery polymers of low molecular weight were obtained with PF~5~ and BF~3~ · OEt~2~ as catalysts, while no polymer was obtained with SbCl~5~ and SnCl~4~ as initiators. The IR, ^1^H and ^13^C NMR spectra of the polymers indicated that they consist of three kinds of repeating units, that is, two unsaturated units caused by ring‐opening polymerization and one addition unit. Using proton NMR data of the polymers, the distribution of repeating units was calculated. A polymerization mechanism is proposed. The thermal stability of the obtained polymers is discussed.

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