The reaction of substituted ethylα-bromocinnamates with tetrabutyl ammonium fluoride  

作　　者：Yan Liang Ying Peng Zhang Wei Yu 

机构地区：[1]School of Petrochemical Engineering,Lanzhou University of Technology,Lanzhou 730050,China [2]State Key Laboratory of Applied Organic Chemistry,Lanzhou University,Lanzhou 730000,China

出　　处：《Chinese Chemical Letters》2012年第7期777-780,共4页中国化学快报（英文版）

摘　　要：The reaction of ethyl α-bromocinnamates with tetrabutyl ammonium fluoride（TBAF） was influenced largely by the position of the substituent at the phenyl ring.While the substrates without an ortho substituent at the phenyl ring were transformed to the corresponding β-fluoro ethyl cinnamates under the reaction conditions,the presence of an ortho substituent only resulted in the formation of ethyl 3-phenylpropiolate derivatives.The reaction of ethyl 2-bromo-3-（4-methoxyphenyl） acrylate also failed to deliver the hydrofluorination product due to the electron-donating effect of the methoxy group.The reaction of ethyl α-bromocinnamates with tetrabutyl ammonium fluoride（TBAF） was influenced largely by the position of the substituent at the phenyl ring.While the substrates without an ortho substituent at the phenyl ring were transformed to the corresponding β-fluoro ethyl cinnamates under the reaction conditions,the presence of an ortho substituent only resulted in the formation of ethyl 3-phenylpropiolate derivatives.The reaction of ethyl 2-bromo-3-（4-methoxyphenyl） acrylate also failed to deliver the hydrofluorination product due to the electron-donating effect of the methoxy group.

关 键 词：Tetrabutyl ammonium fluoride Ethyl α-bromocinnamates Hydrofluorination Elimination 

分 类 号：TQ028.32[化学工程] O623.624[理学—有机化学]