Elemental fluorine .2. Direct fluorination of 1,3-dicarbonyl compounds

被引：69

作者：

Chambers, RD ^{[1
]}

Greenhall, MP ^{[1
]}

Hutchinson, J ^{[1
]}

机构：

[1] UNIV DURHAM,DEPT CHEM,SCI LABS,BNFL FLUOROCHEM LTD,DURHAM RES UNIT,DURHAM DH1 3LE,ENGLAND

来源：

TETRAHEDRON | 1996年 / 52卷 / 01期

关键词：

D O I：

10.1016/0040-4020(95)00883-A

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In acid media, 1,3-diketones and 1,3-ketoesters can be fluorinated in high yield and often with high conversion mainly to the corresponding 2-fluoro- compounds. Diesters such as diethyl malonate do not react with fluorine under the same reaction conditions. The mechanism of these reactions has been investigated and while the identity of the electrophilic fluorinating species is uncertain, we believe that the essential features of the reaction pathway are understood.

引用

页码：1 / 8

页数：8

共 19 条

[1] FLUORONITROALIPHATICS .3. PREPARATION OF SOME NEGATIVELY SUBSTITUTED HALONITROMETHANES [J].

ADOLPH, HG ;

OESTERLI.RE ;

SITZMANN, ME .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (11) :4296-&

[2] N-HALOGENO COMPOUNDS .12. SITE-SPECIFIC FLUORINATION OF CARBANIONS WITH PERFLUORO-N-FLUOROPIPERIDINE [J].

BANKS, RE ;

MURTAGH, V ;

TSILIOPOULOS, E .

JOURNAL OF FLUORINE CHEMISTRY, 1991, 52 (03) :389-401

[3] EFFICIENT ELECTROPHILIC FLUORINATION OF BETA-DICARBONYL COMPOUNDS WITH THE SELECTFLUOR REAGENT F-TEDA-BF4 (1-CHLOROMETHYL-4-FLUORO-1,4-DIAZONIABICYCLO[2.2.2]OCTANE BIS(TETRAFLUOROBORATE)) [J].

BANKS, RE ;

LAWRENCE, NJ ;

POPPLEWELL, AL .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (03) :343-344

[4]

Filler R., 1982, BIOMEDICAL ASPECTS F

[5]

KAGAN HB, 1980, TETRAHEDRON LETT, V21, P277

[6]

MACHLEIDT H, 1964, LIEBIGS ANN CHEM, V679, P9

[7]

MACHLEIDT H, 1969, Patent No. 3435063

[8]

MARCH J, 1985, ADV ORG CHEM, P530

[9] SELECTIVE MONOFLUORINATION OF BETA-DIKETONES [J].

PURRINGTON, ST ;

BUMGARDNER, CL ;

LAZARIDIS, NV ;

SINGH, P .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (19) :4307-4310

[10] ELECTROPHILIC FLUORINATION OF PHARMACOLOGICALLY ACTIVE 1,3-DICARBONYL COMPOUNDS [J].

RESNATI, G ;

DESMARTEAU, DD .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (15) :4281-4284

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