1- AND 2-FLUOROALKYL CARBOXYLATES

被引：0
|
作者：
LIMAT, D [1 ]
GUGGISBERG, Y [1 ]
SCHLOSSER, M [1 ]
机构：
[1] UNIV LAUSANNE,INST CHIM ORGAN,CH-1015 LAUSANNE,SWITZERLAND
来源：
LIEBIGS ANNALEN | 1995年 / 05期
关键词：
ORGANOFLUORINE COMPOUNDS; 1-FLUOROALKYL ESTERS; 2-FLUOROALKYL ESTERS; ENE ESTERS; DIENE ESTERS;
D O I：
暂无
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The 2-fluoroalkyl esters (1-4) of carboxylic acids are readily accessible by the base-catalyzed acylation of fluorohydrines. A two-step procedure is required to prepare the 1-fluoroalkyl esters (10-14, 16): conversion of alk-1-enyl carboxylates (''ene esters'') into the 2-bromo-1-fluoroalkyl esters 5-9, 15, 17-19 by simultaneous treatment with N-bromosuccinimide and hydrogen fluoride followed by the reductive replacement of bromine by tributyltin hydride. Alka-1,3-dienyl carboxylates (''diene esters'') undergo 1,4-addition of bromine and fluorine. The resulting 4-bromo-1-fluoroalk-2-enyl carboxylates 20-25 undergo a substitution reaction with sodium benzenesulfinate to afford the sulfones 26-28 or oxidation with dimethyl sulfoxide to yield the 8-oxo derivatives 29-30.
引用
收藏
页码：849 / 853
页数：5
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