电有机合成1,4-双[2-(3,4,5-三甲氧基苯基)乙烯基]苯的反应条件及机理研究

Studies on the Reaction Conditions and Mechanism of Electroorganic Synthesis of 1,4-Bis[2-(3,4,5-trimethoxyphenyl)vinyl]benzene

1 ,4 双 [2 (3,4,5 三甲氧基苯基 )乙烯基 ]苯 (简称HPV)是导电高分子材料之一 .研究了电极材料、反应电流、溶剂、反应物浓度、反应温度等因素对电化学合成HPV的影响 .实验表明在所有因素中 ,使用混合溶剂对于顺式产物的生成影响最大 ,当使用甲醇和吡啶混合溶剂时可得到 90 %的产率 ,产物中约有 47%的cis cis,48%的cis trans和 5 %的trans trans异构体 ,顺式键与反式键比例约为 2 .4∶1.

1, 4-Bis[2-(3, 4, 5-trimethoxyphenyl)vinyl] benzene (HPV) is one of organic conducting materials. The effect of electro-Wittig synthesis reaction conditions, including the material of the electrode, the reaction current, the type of solvent, the concentration of reactants, the reaction temperature and so on, on the yields and reaction selectivity of the three isomers of HPV is studied. The experimental results show that the use of mixed solvents greatly benefits the formation of cis-isomer in the electrosynthesis of HPV. If a mixed solvents of methanol and pyridine was used, about 47% cis-cis, 48% cis-trans and 5% trans-trams isomers were obtained in 90% yield with a cis : trams ratio of about 2.4:1. The possible reaction mechanism is also discussed.