An efficient dehydrohalogenation method for the synthesis of α,β,β-trifluorostyrenes, α-chloro-β,β-difluorostyrenes and E-1-arylperfluoroalkenes

被引：22

作者：

Anilkumar, R ^{[1
]}

Burton, DJ ^{[1
]}

机构：

[1] Univ Iowa, Dept Chem, Iowa City, IA 52242 USA

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2005年 / 126卷 / 08期

基金：

美国国家科学基金会;

关键词：

1,2,2-trifluorostyrene; 1-chloro-2,2-difluorostyrene; 1-arylperfluoroalkene; 1-aryl-1,2,2,2-tetrafluoroethane; 1-chloro-1-aryl-2,2,2-trifluoroethane; dehydrofluorination; dehydrohalogenation; trifluoromethylketone; LHMDS; DAST;

D O I：

10.1016/j.jfluchem.2005.05.005

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Dehydrofluorination of 1-aryl-1,2,2,2-tetrafluoroethanes (ArCHFCF3) and 1-aryl-1-chloro-2,2,2-trifluoroethane (ArCHClCF3) using lithiumhexamethyldisilazide (LHMDS) in tetrahydrofuran (THF) at room temperature produced 1,2,2-trifluorostyrene and 1-chloro-2,2-difluorostyrene, respectively, in very good isolated yields. Dehydrofluorination of 1,2,2,3,3,3-hexafluoro-1-phenyl-propane (PhCHFCF2CF3) and 1,2,2,3,3,4,4,4-octafluoro-1-phenyl-butane (PhCHFCF2CF2CF3) using LHMDS produced the corresponding substituted olefins (1-phenyl-1,2,3,3,3-pentafluoroprop-1-ene and 1-phenyl-1,2,3,3,4,4,4-pentafluorobut-1-ene) in good yield and high E-selectivity. Dehydrofluorination of 1-chloro-1-phenyl-2,2,3,3,3-pentafluoropropane (PhCHClCF2CF3) and 1-chloro-1-phenyl-2,2,3,3,4,4,4-heptafluorobutane (PhCHClCF2CF2CF3) produced a mixture of the corresponding E and Z olefins (PhCCl=CFCF3 and PhCCl=CFCF2CF3) in good yield. (c) 2005 Elsevier B.V. All rights reserved.

引用

页码：1174 / 1184

页数：11

共 43 条

[1] The first preparation of the α-iodo-β,β-difluorovinylzinc reagent (CF2=CIZnCl) and a high-yield one-pot synthesis of α-iodo-β,β-difluorostyrenes [J].