Abstract
AbstractThe cationic ring‐opening polymerization of 2‐ethenyl‐4‐methylene‐1,3‐dioxolane (3) was carried out. The unsaturated cyclic acetal 3 was prepared by dehydrochlorination of 4‐chloromethyl‐2‐ethenyl‐1,3‐dioxolane, which was readily obtained from acrolein and epichlorohydrin, with sodium methoxide at ambient temperature. The cationic polymerization of 3 with BF3OEt2 or CF3SO3H at −78°C afforded cross‐linked polymers, whereas the polymerization by CH3SO3H gave a soluble poly(keto‐ether) which consisted of a unit containing a carbon‐carbon double bond in the side chain (unit 4) and a unit containing a vinyl ether group in the main chain (unit 5). The reaction of 3 with ethanethiol in the presence of a protic acid was also carried out as a model reaction of the polymerization. The reaction was initiated by addition of a proton to the 4‐methylene group of 3, followed by quantitative ring‐opening isomerization to afford acyclic ketones containing the ethylthio group. On the basis of the model reaction, some speculation on the polymerization mechanism is disclosed.
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