Highly selective hydrohalogenation reaction of substituted 2,3-allenoates  

作　　者：麻生明 王光伟 

出　　处：《Chinese Journal of Chemistry》1999年第5期545-549,428,共5页中国化学（英文版）

基　　金：National Natural Science Foundation of China (No. 29525202);Shanghai Municipal Cormnittee of Science and Technology (No. 98QA14001).

摘　　要：The hydrohalogenation reaction of 1-alkyl substituted 1,2-allenyl carboxylic acid esters (1) with MX (M= Na, or Li, X= Cl, Br, I) afforded a mixture of β,γ-unsaturated 3-halo–3-alkenoates (2) and Q,P unsaturated 3-halo-2-alkenoates (3) in HOAc, while using a mixture of HOAC-CF3CO2H (1:1) or CF3C2H as the reaction medium the corresponding reaction cleanly produced β,γ -unsaturated 3-hale3-alkenoates (2) as the sole products in high yields. The subsequent coupling reactions were studied.The hydrohalogenation reaction of 1-alkyl substituted 1,2-allenyl carboxylic acid esters (1) with MX (M= Na, or Li, X= Cl, Br, I) afforded a mixture of β,γ-unsaturated 3-halo–3-alkenoates (2) and Q,P unsaturated 3-halo-2-alkenoates (3) in HOAc, while using a mixture of HOAC-CF3CO2H (1:1) or CF3C2H as the reaction medium the corresponding reaction cleanly produced β,γ -unsaturated 3-hale3-alkenoates (2) as the sole products in high yields. The subsequent coupling reactions were studied.

关 键 词：Hydrohalogenation 1 2-allenyl carboxylic acid esters β γ-unsaturated 3-halo-3-alkenoates α β-unsaturated 3-halo-2-alkenoates SELECTIVITY 

分 类 号：O621[理学—有机化学]