From alkyl halides to alkyltrifluoromethyls using bromine trifluoride

被引:26
作者
Hagooly, A [1 ]
Ben-David, I [1 ]
Rozen, S [1 ]
机构
[1] Tel Aviv Univ, Raymond & Beverly Sackler Fac Exact Sci, Sch Chem, IL-69978 Tel Aviv, Israel
关键词
D O I
10.1021/jo026128b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Under the right conditions, bromine trifluoride can be a useful tool for generating new types of reactions and compounds. Thus, tris(methylthio)alkyl derivatives, easily prepared from the corresponding alkyl bromides, were converted to the corresponding RCHBrCF2SMe or RCHBrCF3 compounds. The bromine atom, however, could be easily reduced forming eventually R'CF2SMe or R'CF3. If desired, the bromine atom can serve as an entry for constructing terminal difluoroolefins.
引用
收藏
页码:8430 / 8434
页数:5
相关论文
共 23 条
[1]   Supersonic gas chromatography/mass spectrometry [J].
Amirav, A ;
Gordin, A ;
Tzanani, N .
RAPID COMMUNICATIONS IN MASS SPECTROMETRY, 2001, 15 (10) :811-820
[2]   A novel synthesis of trifluoromethyl ethers via xanthates, utilizing BrF3 [J].
Ben-David, I ;
Rechavi, D ;
Mishani, E ;
Rozen, S .
JOURNAL OF FLUORINE CHEMISTRY, 1999, 97 (1-2) :75-78
[3]  
BOGUSLAVSKAYA LS, 1989, ZH ORG KHIM, V25, P1835
[4]   ELECTRON-IMPACT MASS-SPECTROMETRY OF ALKANES IN SUPERSONIC MOLECULAR-BEAMS [J].
DAGAN, S ;
AMIRAV, A .
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, 1995, 6 (02) :120-131
[5]  
FUCHIGAMI T, 1998, Patent No. 10287596
[6]   Fluorination of orthothioesters through oxidative desulfurization-fluorination [J].
Furuta, S ;
Kuroboshi, M ;
Hiyama, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1998, 71 (08) :1939-1951
[7]   2,2,2-Trifluoroethyl iodide [J].
Gilman, H ;
Jones, RG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1943, 65 :2037-2038
[8]  
Halpern D.F., 1991, US patent, Patent No. [US 4996371A, 4996371, 4,996,371]
[9]   A new route to 1,1-difluoroolefins from carboxylic acids [J].
Kim, KI ;
McCarthy, JR .
TETRAHEDRON LETTERS, 1996, 37 (19) :3223-3226
[10]  
KOBAYASHI Y, 1979, TETRAHEDRON LETT, P4071