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))

被引：91

作者：

BANKS, RE

LAWRENCE, NJ

POPPLEWELL, AL

机构：

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1994年 / 03期

关键词：

D O I：

10.1039/c39940000343

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

1,3-Dicarbonyl compounds (acyclic and cyclic 1,3-diketones, beta-ketoesters, beta-ketoamides) are converted efficiently to 2-monofluoro derivatives, and thence to 2,2-difluoro derivatives, with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate).

引用

页码：343 / 344

页数：2

共 26 条

[1] OXIDATION OF BENZYLIC ALCOHOLS AND BENZALDEHYDES WITH THE SELECTFLUOR(TM) REAGENT F-TEDA-BF4 (1-CHLOROMETHYL-4-FLUORO-1,4-DIAZONIABICYCLO[2.2.2]OCTANE BIS(TETRAFLUOROBORATE))
BANKS, RE
LAWRENCE, NJ
POPPLEWELL, AL
SYNLETT, 1994, (10) : 831 - 832
[2] Recent highlights in electrophilic fluorination with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)
Singh, RP
Shreeve, JM
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (01) : 31 - 44
[3] N-Halogeno compounds.: Part 20.: Vicarious electrophilic fluorodemethylation of 1,3,5-trimethoxybenzene and 2,4,6-trimethoxytoluene with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor™ reagent F-TEDA-BF4)
Banks, RE
Besheesh, MK
Górski, RW
Lawrence, NJ
Taylor, AJ
JOURNAL OF FLUORINE CHEMISTRY, 1999, 96 (02) : 129 - 133
[4] Synthesis of α-fluorinated phosphonoacetate derivatives using electrophilic fluorine reagents:: Perchloryl fluoride versus 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor®)
Marma, MS
Khawli, LA
Harutunian, V
Kashemirov, BA
McKenna, CE
JOURNAL OF FLUORINE CHEMISTRY, 2005, 126 (11-12) : 1467 - 1475
[5] STRUCTURE OF THE NEW ELECTROPHILIC FLUORINATING AGENT 1-CHLOROMETHYL-4-FLUORO-1,4-DIAZONIABICYCLO[2.2.2]OCTANE BIS(TETRAFLUOROBORATE) AND 2 OF ITS MONOQUATERNARY ANALOGS
BANKS, RE
SHARIF, I
PRITCHARD, RG
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1993, 49 : 492 - 495
[6] Effect of cycloalkene structure on fluorination with 1-chloromethyl-4-fluoro-1,4-diazonia[2.2.2]octane bis(tetrafluoroborate) (F-TEDA)
Zupan, M
Skulj, P
Stavber, S
TETRAHEDRON, 2001, 57 (50) : 10027 - 10031
[7] 1-HYDROXYL-4-FLUORO-1,4-DIAZONIABICYCLO[2.2.2]OCTANE BIS(TETRAFLUOROBORATE) - AN ELECTROPHILIC FLUORINATING AGENT
POSS, AJ
SHIA, GA
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 210 : 52 - ORGN
[8] 1-Fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate): An electrophilic fluorinating agent
Poss, AJ
Shia, GA
TETRAHEDRON LETTERS, 1999, 40 (14) : 2673 - 2676
[9] Direct α-iodination of aryl alkyl ketones by elemental iodine activated by 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)
Jereb, Marjan
Stavber, Stojan
Zupan, Marko
Synthesis, 2003, (06) : 853 - 858
[10] Direct α-lodination of aryl alkyl ketones by elemental iodine activated by 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)
Jereb, M
Stavber, S
Zupan, M
SYNTHESIS-STUTTGART, 2003, (06): : 853 - 858

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