Nucleophilic routes to selectively fluorinated aromatics

被引:162
作者
Adams, DJ [1 ]
Clark, JH [1 ]
机构
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
关键词
D O I
10.1039/a808707e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Selectively fluorinated aromatic compounds are of interest in many sectors. Of the methodologies used for their formation, halogen exchange is the only industrial rival to the diazonium based routes, Although many compounds can be formed by halogen exchange, the formation of meta-fluorinated species by this route is difficult, One possible method for overcoming this is fluorodenitration, Although traditionally plagued by side reactions, recent reports suggest that, with careful control of the reaction conditions, fluorodenitration could well provide a viable industrial alternative for the formation of selectively fluorinated aromatic compounds.
引用
收藏
页码:225 / 231
页数:7
相关论文
共 34 条
[1]   Unexpected side products in the tetramethylammonium fluoride-dimethylsulphoxide system [J].
Adams, DJ ;
Clark, JH ;
McFarland, H ;
Nightingale, DJ .
JOURNAL OF FLUORINE CHEMISTRY, 1999, 94 (01) :51-55
[2]   The formation of 4,4′-difluorobenzophenone from 4,4′-dinitrodiphenylmethane [J].
Adams, DJ ;
Clark, JH ;
McFarland, H .
JOURNAL OF FLUORINE CHEMISTRY, 1998, 92 (02) :127-129
[3]  
ADAMS DJ, IN PRESS TETRAHEDRON
[4]   DISPLACEMENT OF A NITRO-GROUP BY [F-18]-LABELED FLUORIDE-ION - A NEW ROUTE TO ARYL FLUORIDES OF HIGH SPECIFIC ACTIVITY [J].
ATTINA, M ;
CACACE, F ;
WOLF, AP .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (03) :108-109
[5]   SELECTIVE FLURODENITRATION OF CHLORONITROAROMATICS [J].
BEAUMONT, AJ ;
CLARK, JH ;
BOECHAT, NA .
JOURNAL OF FLUORINE CHEMISTRY, 1993, 63 (1-2) :25-30
[6]   NUCLEOPHILIC DISPLACEMENT OF AROMATIC NITRO-GROUPS [J].
BECK, JR .
TETRAHEDRON, 1978, 34 (14) :2057-2068
[7]   FLUORODENITRATIONS USING TETRAMETHYLAMMONIUM FLUORIDE [J].
BOECHAT, N ;
CLARK, JH .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (11) :921-922
[8]   SYNTHESIS OF N-TERT-BUTYL-ALPHA-(4-[F-18]FLUOROPHENYL)NITRONE ([F-18]FPBN) FOR IN-VIVO DETECTION OF FREE-RADICALS [J].
BORMANS, G ;
KILBOURN, MR .
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1995, 36 (02) :103-110
[9]   THE FLUORINATION OF ORGANIC SUBSTRATES WITH TETRAPHENYLPHOSPHONIUM HYDROGENDIFLUORIDE [J].
BROWN, SJ ;
CLARK, JH .
JOURNAL OF FLUORINE CHEMISTRY, 1985, 30 (03) :251-258
[10]  
BUNCEL E, 1982, CHEM AMINO NITROSO N