Application of 1-(3-bromo-3,3-difluoroprop-1-ynyl)benzenes in Diels-Alder reactions:: Synthesis of ortho-CF2Br-substituted biaryls

被引:7
作者
Muzalevskiy, Vasilly M. [1 ]
Nenajdenko, Valentine G. [1 ]
Shastin, Aleksey V. [2 ]
Balenkova, Elizabeth S. [1 ]
Haufe, Guenter [3 ]
机构
[1] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119992, Russia
[2] Inst Problems Chem Phys, Chernogolovka 142432, Moscow Region, Russia
[3] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany
来源
SYNTHESIS-STUTTGART | 2008年 / 18期
关键词
alkynes; biaryls; bicyclic compounds; Diels-Alder reaction; fluorine;
D O I
10.1055/s-2008-1067221
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1-(3-Bromo-3,3-difluoroprop-1-ynyl)benzenes were found to be good dienophiles in Diels-Alder reactions. Based oil this key reaction a new pathway towards biaryls with an ortho-CF2Br group was elaborated.
引用
收藏
页码:2899 / 2904
页数:6
相关论文
共 66 条
[21]  
Ernst JT, 2002, ANGEW CHEM INT EDIT, V41, P278, DOI 10.1002/1521-3773(20020118)41:2<278::AID-ANIE278>3.0.CO
[22]  
2-A
[23]   Diastereoselective Diels-Alder reactions of α-fluorinated α,β-unsaturated carbonyl compounds:: Chemical consequences of fluorine substitution.: 2. [J].
Essers, M ;
Mück-Lichtenfeld, C ;
Haufe, G .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (14) :4715-4721
[24]  
Filler R., 1993, ORGANOFLUORINE COMPO
[25]  
Fringuelli F., 1990, Dienes in the Diels-Alder Reaction
[26]   A convenient synthesis and chemical properties of 3-acylamino-6-polyfluoroalkyl-2H-pyran-2-ones [J].
Gerus, II ;
Tolmachova, NA ;
Vdovenko, SI ;
Fröhlich, R ;
Haufe, G .
SYNTHESIS-STUTTGART, 2005, (08) :1269-1278
[27]   [4+2]-CYCLOADDITION REACTIONS EMPLOYING 2-FLUORO-2-ALKENAL N,N-DIMETHYLHYDRAZONES - SYNTHESIS OF 3-FLUOROPYRIDINES AND DIHYDRO OR TETRAHYDRO DERIVATIVES THEREOF [J].
GHOSH, S ;
SCHLOSSER, M .
JOURNAL OF FLUORINE CHEMISTRY, 1994, 67 (01) :53-56
[28]  
HAIDUCH J, 2007, EUR J ORG CHEM, P5101
[29]  
HAUFE G, 2005, VINYL FLUORIDES CYCL, P155
[30]  
HIYAMA T, 1990, SYNLETT, P53