三苯基膦乙烯基-4-苯甲酸Wittig反应活性研究

Research on Three Phenyl phosphonite Vinyl-4-benzoic Acid Wittig Reactivity

目的:探讨不同取代羰基化合物与三苯基膦乙烯基-4-苯甲酸发生Wittig反应的条件,优化生产工艺,为合成不同取代烯烃提供研究基础。方法:对氯甲基苯甲酸与三苯基膦反应生成季鏻盐,季鏻盐在强碱(如正丁基锂、苯基锂、乙醇钠等)的作用下脱去1分子的卤代烃,得到三苯基膦乙烯基-4-苯甲酸(以下简称Wittig试剂),得到的Wittig试剂与不同的醛、酮发生Wittig发应。结果:Wittig试剂与甲醛、5-硝基糠醛和苯甲醛发生Wittig反应,而与丙酮、丁酮不发生Wittig反应。结论:只与醛发生Wittig反应,不与酮发生反应;实验结果表明醛的反应活性大于酮。

Objective： Studying the different substitution carbonyl compounds with three phenyl phosphonite vinyl-4-benzoic acid happen Wittig reaction conditions. Optimizing production processes and synthesizing different provides research foundation replaced olefins. Methods： P-chlorine methyl benzoic acid reacts with Triphenylphosphin to produce Tributyl Tetradecyl Phospbonium Chloride（TTPC）. TTPC will remove 1 molecular HCI to get three phenyl phosphonite vinyl-4-benzoic acid when it is in alkaline condition （such as n- butyl lithium, Phenyl lithium, caustic alcohol etc）. Then the Wittig reagents will reat with different aldehydes and ketones. Results： Three phenyl phosphonite vinyl-4-benzoic acid with formaldehyde, 5-nitro furfural, benzaldehyde can happen Wittig reactions, but it can not occur with acetone and butanone. Conclusion： Only aldehyde can reat with three phenyl phosphonite vinyl-4-benzoic acid and ketone can＇t. The aldehyde active than ketone.