A MILD, SELECTIVE METHOD FOR PREPARATION OF VICINAL FLUORO ETHERS USING F-TEDA-BF4

被引:43
作者
STAVBER, S [1 ]
SOTLER, T [1 ]
ZUPAN, M [1 ]
机构
[1] UNIV LJUBLJANA,DEPT CHEM,LJUBLJANA 61000,SLOVENIA
关键词
D O I
10.1016/S0040-4039(00)79977-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Vicinal alkoxy fluorides are efficiently formed by room temperature reaction of phenyl substituted alkenes with commercially available 1-chloromethyl-4-fluoro-1,4-diazobicyclo[2.2.2]octane bis tetrafluoroborate (Selectfluor(TM) F-Teda BF4) in CH3CN in the presence of various alcohols. The reaction follows Markovnikov-type regioselectivity, while stereoselectivity in the case of phenyl substituted benzocyclenes strongly depends on the ring size and the structure of the alcohol.
引用
收藏
页码:1105 / 1108
页数:4
相关论文
共 24 条
[1]  
Banks R.E., 1992, US Patent, Patent No. [5086178, 5,086,178]
[2]   1-ALKYL-4-FLUORO-1,4-DIAZONIABICYCLO[2.2.2]OCTANE SALTS - A NOVEL FAMILY OF ELECTROPHILIC FLUORINATING AGENTS [J].
BANKS, RE ;
MOHIALDINKHAFFAF, SN ;
LAL, GS ;
SHARIF, I ;
SYVRET, RG .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (08) :595-596
[3]  
BANKS RE, 1986, FLUORINE 1ST 100 YEA
[4]   N-FLUOROBIS[(PERFLUOROALKYL)SULFONYL]IMIDES - REACTIONS WITH SOME OLEFINS VIA ALPHA-FLUORO CARBOCATIONIC INTERMEDIATES [J].
DESMARTEAU, DD ;
XU, ZQ ;
WITZ, M .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (02) :629-635
[5]   ELECTROCHEMICAL REDUCTION OF NITROGEN-FLUORINE BONDS - RELEVANCE TO THE REACTIVITY OF ELECTROPHILIC FLUORINATING AGENTS [J].
DIFFERDING, E ;
BERSIER, PM .
TETRAHEDRON, 1992, 48 (09) :1595-1604
[6]   SYNTHESIS OF 5-FLUOROPROSTACYCLIN [J].
DJURIC, SW ;
GARLAND, RB ;
NYSTED, LN ;
PAPPO, R ;
PLUME, G ;
SWENTON, L .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (06) :978-990
[7]   BROMINATION OF CYCLIC OLEFINS .I. CRITICAL DEPENDENCE OF CARBONIUM ION STABILITY ON COPALNARIRY [J].
DUBOIS, JE ;
HEGARTY, AF .
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1969, (06) :638-&
[8]  
Filler R., 1982, BIOMEDICAL ASPECTS F
[9]  
German L., 1989, NEW FLUORINATING AGE
[10]   SYNTHESIS OF FLUORO ETHERS WITH ACETYL HYPOFLUORITE [J].
HEBEL, D ;
ROZEN, S .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12) :2588-2590