Structure and Reactivity of α,β-Unsaturated Ethers. XI. Cationic Copolymerization and Acetal Addition of <I>cis</I>- and <I>trans</I>-Sthyl Ethyl Ethers
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概要
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The cationic copolymerization between <I>cis</I>- and <I>trans</I>-styryl ethyl ethers in methylene chloride was investigated in the temperature range from −70 to 0°C with boron trifluoride etherate as catalyst. It was found that at lower temperatures the <I>trans</I> ether is more reactive than its <I>cis</I> isomer, although the relative reactivities are reversed at 0°C. Addition reactions of various acetals to <I>cis</I>- and <I>trans</I>-styryl ethyl ethers were carried out at 0°C with the same Lewis acid as catalyst. The relative <I>cis</I>-<I>trans</I> reactivities are largely dependent on the bulkiness of an attacking oxycarbonium ion. It was concluded that the <I>cis</I> isomer, which is electronically more reactive toward cations, is liable to suffer adverse steric effect, especially when the attacking carbonium ion is bulky.
- 公益社団法人 日本化学会の論文
著者
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Fueno Takayuki
Faculty Of Engineering Science Osaka University
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Okuyama Tadashi
Faculty Of Engineering Science Osaka University
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Asami Nobuhiro
Faculty of Engineering Science, Osaka University
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