Abstract
The ring-opening polymerization behavior of five-membered lactones fused to a cyclohexane ring (that is, the trans- and cis-hexahydro-2(3H)-benzofuranone denoted T6L and C6L, respectively) was investigated under various conditions. The potassium tert-butoxide (tBuOK)-initiated anionic polymerization of T6L yields polymers with number-average molecular weight (Mn) values of 5000. However, no polymeric products were obtained via cationic and coordination polymerization. Among the anionic initiators, a base stronger than an alkoxide initiated the polymerization of T6L. In contrast, cis-isomer C6L did not polymerize regardless of the initiator species used, which implied an increase in the ring strain of the lactone ring by the trans-fused cyclohexane. The anionic polymerization of T6L was reversible, and the thermodynamic parameters characterizing the polymerization of T6L were estimated to be ΔHp°=−18 kJ·mol−1 and ΔSp°=–65 J·K−1mol−1 on the basis of the measurement of the equilibrium monomer concentration.
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We thank Professor Seigou Kawaguchi from Yamagata University for his helpful advice regarding the density measurements.
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Haba, O., Itabashi, H. Ring-opening polymerization of a five-membered lactone trans-fused to a cyclohexane ring. Polym J 46, 89–93 (2014). https://doi.org/10.1038/pj.2013.70
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DOI: https://doi.org/10.1038/pj.2013.70
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