To suppress intermolecular propagation by steric hindrance of monomer substituents and increase cyclopolymerization tendency thereby, two bulky tert‐butyl groups are introduced to the benzene ring of 1,2‐bis(2‐vinyloxyethoxy)benzene (1), which is a representative monomer for cationic cyclopolymerization of divinyl ethers. Thus, 3,5‐di‐tert‐butyl‐1,2‐bis(2‐vinyloxyethoxy)benzene (2) was synthesized and polymerized with the HCl/ZnCl2 initiating system in CH2Cl2 at −15 °C ([Monomer]0 = 0.15 M) to produce completely soluble polymers quantitatively. The vinyl content of the polymer obtained in the early stage of the polymerization (17% monomer conversion) was 4.0 mol %; in other words, its degree of cyclization was 96%. The cyclopolymerization tendency of 2 was found to be higher than that of 1 (the degree of cyclization, 93%; under the same conditions).
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