Kasashima Yoshio, Uzawa Atsushi, Hashimoto Kahoko, Nishida Tadasuke, Murakami Keiko, Mino Takashi, Sakamoto Masami, Fujita Tsutomu
Education Center, Faculty of Engineering, Chiba Institute of Technology, Chiba, Japan.
J Oleo Sci. 2010;59(10):549-55. doi: 10.5650/jos.59.549.
Reactions of α-vinylbenzyl alcohol with other alcohols using iodine as a catalyst were investigated. The corresponding cinnamyl ethers were obtained as products. This suggested that α-vinylbenzyl alcohol was converted to cinnamyl ethers via 1-phenylallyl cation. Cinnamyl ethyl ether was obtained in 75% yield by the reaction of α-vinylbenzyl alcohol and ethanol in acetonitrile with iodine under the following conditions: temperature = 50 °C, molar ratio of α-vinylbenzyl alcohol:ethanol:iodine = 1:3.0:0.2, and time period = 6 h. Generally, the yields of the reactions using primary alcohols were higher than those using secondary and tertiary alcohols. Ether interchange also occurred by the reaction of α-vinylbenzyl alcohol and iodine, but proceeded smoothly only when an allyl group was used as the other substituent of the starting ether.
研究了以碘为催化剂时，α-乙烯基苄醇与其他醇类的反应。得到了相应的肉桂基醚作为产物。这表明α-乙烯基苄醇通过1-苯基烯丙基阳离子转化为肉桂基醚。在以下条件下，α-乙烯基苄醇与乙醇在乙腈中与碘反应，以75%的产率得到肉桂基乙醚：温度 = 50 °C，α-乙烯基苄醇:乙醇:碘的摩尔比 = 1:3.0:0.2，反应时间 = 6 h。一般来说，使用伯醇的反应产率高于使用仲醇和叔醇的反应产率。α-乙烯基苄醇与碘的反应也会发生醚交换，但只有当烯丙基用作起始醚的另一个取代基时，反应才能顺利进行。
