Catalytic hunsdiecker reaction of α,β-unsaturated carboxylic acids:: How efficient is the catalyst?

被引:110
作者
Das, JP [1 ]
Roy, S [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Organomet & Catalysis Lab, Kharagpur 721302, W Bengal, India
关键词
D O I
10.1021/jo025868h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
UV-vis spectrophotometry is utilized to measure the relative efficiency of lithium acetate, tetrabutylammonium. trifluoroacetate, and triethylamine as catalysts for the conversion of 4-methoxycinnamic acid to 4-methoxy-beta-bromostyrene. In acetonitrile-water as solvent, the efficiency order is lithium acetate > triethylamine > tetrabutylammonium trifluoroacetate. For triethylamine as catalyst, solvent-dependent order is acetonitrile-water > dichloromethane > acetonitrile. Using triethylamine as catalyst (5-20 mol %), cinnamic acids, and propiolic acids are converted to corresponding beta-bromostyrenes and 1-halo-1-alkynes in 60-98% isolated yields within 1-5 min.
引用
收藏
页码:7861 / 7864
页数:4
相关论文
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