REACTION OF BUCKMINSTERFULLERENE WITH ORTHO-QUINODIMETHANE - A NEW ACCESS TO STABLE C60 DERIVATIVES

被引:240
作者
BELIK, P [1 ]
GUGEL, A [1 ]
SPICKERMANN, J [1 ]
MULLEN, K [1 ]
机构
[1] MAX PLANCK INST POLYMER RES,ACKERMANNWEG 10,W-6500 MAINZ,GERMANY
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1993年 / 32卷 / 01期
关键词
D O I
10.1002/anie.199300781
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The stable diene adduct 1 can be prepared in(~)good yield when C60 is treated with o-quinodimethane in toluene. o-Quinodimethane is generated in situ from 1,2-bis(bromomethyl)benzene and KI in the presence of [18]crown-6 as phase-transfer catalyst. Adduct 1 was isolated after gel-permeation chromatography, and characterized by mass spectrometry and NMR spectroscopy; the sketch shows its geometry-optimized structure.(~)[GRAPHICS]
引用
收藏
页码:78 / 80
页数:3
相关论文
共 28 条
  • [1] BECK H, 1991, MOMO VERSION 1 0
  • [2] CONDENSED CYCLOBUTANE AROMATIC SYSTEMS .2. DIHALO DERIVATIVES OF BENZOCYCLOBUTENE AND BENZOCYCLOBUTADIENE DIMER
    CAVA, MP
    NAPIER, DR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (07) : 1701 - 1705
  • [3] CONDENSED CYCLOBUTANE AROMATIC COMPOUNDS .8. THE MECHANISM OF FORMATION OF 1,2-DIBROMOBENZOCYCLOBUTENE - A NEW DIELS-ALDER SYNTHESIS
    CAVA, MP
    DEANA, AA
    MUTH, K
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (24) : 6458 - 6460
  • [4] ORTHOQUINODIMETHANES
    CHARLTON, JL
    ALAUDDIN, MM
    [J]. TETRAHEDRON, 1987, 43 (13) : 2873 - 2889
  • [5] SYNTHESES OF BENZO[1,2-4,5]DICYCLOBUTENE DERIVATIVES
    GRAY, R
    HARRUFF, LG
    KRYMOWSKI, J
    PETERSON, J
    BOEKELHEIDE, V
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (09) : 2892 - 2893
  • [6] PREPARATIVE-SCALE SEPARATION OF C-60 AND C-70 ON POLYSTYRENE GEL
    GUGEL, A
    BECKER, M
    HAMMEL, D
    MINDACH, L
    RADER, J
    SIMON, T
    WAGNER, M
    MULLEN, K
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (05): : 644 - 645
  • [7] GUGEL A, 1992, ANGEW CHEM, V104, P666
  • [8] ELECTRONIC-STRUCTURE, CONDUCTIVITY, AND SUPERCONDUCTIVITY OF ALKALI-METAL DOPED C-60
    HADDON, RC
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (03) : 127 - 133
  • [9] CRYSTAL-STRUCTURE OF OSMYLATED C60 - CONFIRMATION OF THE SOCCER BALL FRAMEWORK
    HAWKINS, JM
    MEYER, A
    LEWIS, TA
    LOREN, S
    HOLLANDER, FJ
    [J]. SCIENCE, 1991, 252 (5003) : 312 - 313
  • [10] TITRATION OF C-60 - A METHOD FOR THE SYNTHESIS OF ORGANOFULLERENES
    HIRSCH, A
    SOI, A
    KARFUNKEL, HR
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (06): : 766 - 768