A simple high-yielding synthesis of ferrocene-1',-diylbis-(methyltrimethylammonium iodide)

被引:21
作者
Glidewell, C
Royles, BJL
Smith, DM
机构
[1] School of Chemistry, University of St. Andrews, St. Andrews
基金
英国工程与自然科学研究理事会;
关键词
ferrocene; sodium phenoxide; iodomethane;
D O I
10.1016/S0022-328X(96)06644-2
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A new simple, high-yielding procedure has been developed for the synthesis of ferrocene-1, 1'-diylbis(methyltrimethylammonium iodide) 2. Ferrocene is dilithiated using n-butyllithium/TMEDA and then reacted with Eschenmoser's salt to form the bis(dimethylaminomethyl) derivative 6 in good yield. Treatment with iodomethane gives rise to the corresponding ammonium salt 2 in excellent yield. Reaction of this bis-ammonium salt with sodium phenoxide affords the 1, 1'-bis(phenoxymethyl) compound 10.
引用
收藏
页码:259 / 261
页数:3
相关论文
共 21 条
  • [1] AN IMPROVED SYNTHESIS OF FERROCENE-1,1'-DICARBALDEHYDE
    BALAVOINE, GGA
    DOISNEAU, G
    FILLEBEENKHAN, T
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 412 (03) : 381 - 382
  • [2] SELECTIVE ELECTROCHEMICAL RECOGNITION OF THE POTASSIUM GUEST CATION IN THE PRESENCE OF SODIUM AND MAGNESIUM-IONS BY A NEW FERROCENYL IONOPHORE
    BEER, PD
    SIKANYIKA, H
    BLACKBURN, C
    MCALEER, JF
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (23) : 1831 - 1833
  • [3] 1,1'-BIS[(ALKYL/ARYL)PHOSPHINO]FERROCENES - SYNTHESIS AND METAL-COMPLEX FORMATION - CRYSTAL-STRUCTURE OF 3 METAL-COMPLEXES OF FE(ETA-5-C5H4PPH2)2-
    BUTLER, IR
    CULLEN, WR
    KIM, TJ
    RETTIG, SJ
    TROTTER, J
    [J]. ORGANOMETALLICS, 1985, 4 (06) : 972 - 980
  • [4] THE STRUCTURE OF THE 3-2 ADDUCT OF 1,1'-DILITHIOFERROCENE WITH TETRAMETHYLETHYLENEDIAMINE
    BUTLER, IR
    CULLEN, WR
    NI, J
    RETTIG, SJ
    [J]. ORGANOMETALLICS, 1985, 4 (12) : 2196 - 2201
  • [5] CARLSTROM AS, 1990, J ORG CHEM, V55, P4174
  • [6] CARROLL MA, 1994, SYNLETT, P1025
  • [7] STRUCTURE OF THE HYDROGENATION CATALYST [(P-P)RH(NBD)]CLO4, P-P = (ETA-5-[(CH3)3C]2PC5H4)2FE, AND SOME COMPARATIVE RATE STUDIES
    CULLEN, WR
    KIM, TJ
    EINSTEIN, FWB
    JONES, T
    [J]. ORGANOMETALLICS, 1983, 2 (06) : 714 - 719
  • [8] STRUCTURES OF (FERROCENYLMETHYL)TRIMETHYLAMMONIUM IODIDE AND HEXA-N-METHYLFERROCENE-1,1'-DIYLBIS(METHYLAMMONIUM IODIDE)
    FERGUSON, G
    GALLAGHER, JF
    GLIDEWELL, C
    ZAKARIA, CM
    [J]. ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1994, 50 : 146 - 150
  • [9] SOME SUBSTITUTED CYCLOPENTADIENYL DERIVATIVES OF NICKEL, COBALT, IRON, MOLYBDENUM, AND TITANIUM
    KNOX, GR
    MUNRO, JD
    PAUSON, PL
    SMITH, GH
    WATTS, WE
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1961, (OCT): : 4619 - +
  • [10] Lednicer D., 1960, ORG SYNTH, V40, P31, DOI [10.15227/orgsyn.040.0031, DOI 10.15227/ORGSYN.040.0031]