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Living Cationic Ring-Opening Homo- and Copolymerization of Cyclohexene Oxide by “Dormant” Species Generation Using Cyclic Ethers as Lewis Basic Additives

The living cationic ring-opening polymerization of cyclohexene oxide (CHO) was demonstrated to proceed using cyclic ethers as Lewis basic additives that potentially form “dormant” species through a reaction with the CHO-derived propagating species. The polymers obtained under suitable conditions had molecular weights close to the theoretical values and narrow molecular weight distributions. The formation of the dormant species was strongly supported by the generation of chain ends consisting of a cyclic ether additive and a quencher fragment, which was confirmed by 1H NMR and ESI-MS analysis of the product polymers. The use of additives with appropriate basicity, such as hexamethylene oxide and tetrahydropyran, is of considerable importance for living polymerization. In addition, the living copolymerization of CHO and 1,4-epoxycyclohexene and the synthesis of alternating-like acid-degradable polymers with aliphatic aldehydes were also achieved.

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