N-HALOGENO COMPOUNDS .14. TRANSFER FLUORINATION OF QUINUCLIDINE USING F-TEDA-BF4 (SELECTOR(TM) REAGENT) - LABORATORY SYNTHESIS OF N-FLUOROQUINUCLIDINIUM SALTS NOT REQUIRING THE USE OF ELEMENTAL FLUORINE

被引:36
作者
ABDULGHANI, M
BANKS, RE
BESHEESH, MK
SHARIF, I
SYVRET, RG
机构
[1] UNIV MANCHESTER,INST SCI & TECHNOL,DEPT CHEM,MANCHESTER M60 1QD,LANCS,ENGLAND
[2] AIR PROD & CHEM INC,CTR CORP SCI & TECHNOL,ALLENTOWN,PA 18195
关键词
N-HALOGENO COMPOUNDS; QUINUCLIDINE; SYNTHESIS;
D O I
10.1016/0022-1139(94)03225-O
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
N-Fluoroquinuclidinium tetrafluoroborate (Ib) has been prepared in excellent yield by ''transfer fluorination'' of quinuclidine with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo [ 2.2.2] octanebis(tetrafluoroborate) (F-TEDA BF4, Selectfluor(TM) reagent), which will also effect N-fluorination of pyridine and 2,4,6-trimethylpyridine.
引用
收藏
页码:255 / 257
页数:3
相关论文
共 12 条
[1]   N-HALOGENO COMPOUNDS .13. N-FLUOROQUINUCLIDINIUM SALTS - SYNTHESIS AND USE AS ELECTROPHILIC FLUORINATING AGENTS [J].
BANKS, RE ;
SHARIF, I .
JOURNAL OF FLUORINE CHEMISTRY, 1991, 55 (02) :207-214
[2]   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 [J].
BANKS, RE ;
SHARIF, I ;
PRITCHARD, RG .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1993, 49 :492-495
[3]   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
[4]   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
[5]  
BANKS RE, 1988, J CHEM SOC P1, P205
[6]   ON THE RELATIVE POWER OF ELECTROPHILIC FLUORINATING REAGENTS OF THE N-F CLASS [J].
GILICINSKI, AG ;
PEZ, GP ;
SYVRET, RG ;
LAL, GS .
JOURNAL OF FLUORINE CHEMISTRY, 1992, 59 (01) :157-162
[7]  
LAL GS, 1993, Patent No. 5233074
[8]  
PEZ GP, UNPUB
[9]   ORDERING OF ELECTROPHILIC FLUORINATING REAGENTS OF THE N-F CLASS [J].
SUDLOW, K ;
WOOLF, AA .
JOURNAL OF FLUORINE CHEMISTRY, 1994, 66 (01) :9-11
[10]   PREPARATION OF 2-FLUOROPYRIDINES VIA BASE-INDUCED DECOMPOSITION OF N-FLUOROPYRIDINIUM SALTS [J].
UMEMOTO, T ;
TOMIZAWA, G .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) :1726-1731