Abstract
In order to ascertain the relative reactivity of trimethylsilyl vinyl ether among vinyl ethers, cationic copolymerizations were carried out. Relative rates in bromine addition to the double bonds of vinyl ethers and relative stabilities of the iodine complexes were also studied as related reactions.n-, i-, and t-Butyl vinyl ethers were increasingly reactive in this order in all of these reactions. The reactivity of trimethylsilyl vinyl ether was between the i- and t-butyl vinyl ethers in both the copolymerization and iodine-complex formations, and at its lowest in the bromine addition.The reactivities of trimethylsilyl vinyl ether are rationalized by considering the contribution of the inductive effect of the trimethylsilyl group as well as the various degrees of participation of silicon 3d orbital in stabilizing the transition states.
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