Abstract
AbstractA spectroscopic (UV, IR, 1H NMR) study of the cationic polymerisation of 2‐vinylfuran (1a) and 2‐isopropenylfuran (2a) showed the existence of an important alkylation reaction at C5 which competes with normal propagation. The extent of this competition depends on the monomer used and the polymerisation temperature. A comparison of the spectra of standard polymers (prepared by radical or stereospecific polymerisation) with those of polymers obtained by cationic initiation allowed to assess the extent of alkylation and its regiospecificity at C5 2‐Methyl‐5‐vinylfuran (1b) and 2‐methyl‐5‐isopropenylfuran (2b) were found to undergo cationic polymerisation without any interference from alkylation reactions. Reactions between these four monomers and 2‐methylfuran in the presence of typical acidic catalysts gave very high yields of alkylated products and no polymerisation, thus confirming the importance of this electrophilic reaction and its possible application to synthetic uses.
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