CHEMICAL-TRANSFORMATIONS ON THE SURFACE OF [60]FULLERENE - SYNTHESIS OF [60]FULLERENO[1',2'/4,5]OXAZOLIDIN-2-ONE

被引:55
作者
BANKS, MR
CADOGAN, JIG
GOSNEY, I
HODGSON, PKG
LANGRIDGESMITH, PRR
MILLAR, JRA
TAYLOR, AT
机构
[1] UNIV LONDON IMPERIAL COLL SCI TECHNOL & MED,DEPT CHEM,LONDON SW7 2AY,ENGLAND
[2] BP INT LTD,RES & ENGN CTR,SUNBURY TW16 7LN,MIDDX,ENGLAND
关键词
D O I
10.1016/0040-4039(94)88429-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Base-induced alpha-elimination from substituted O-4-nitrophenylsulfonylhydroxamic acids has been used as a mild source of nitrenes for capture by [60]fullerene; rearrangment of the resulting [60]fullereno[1',2':2,3]aziridine bearing a N-ethoxycarbonyl grouping under the influence of phenol/chlorotrimethylsilane results in the quantitative formation of the title compound which can be cleaved to yield 1-hydroxy-2-N-methylamino[60]fullerene.
引用
收藏
页码:9067 / 9070
页数:4
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共 26 条
  • [1] SYNTHESIS OF ALPHA-AMINO-ACID DERIVATIVES OF C-60 FROM 1,9-(4-HYDROXYCYCLOHEXANO)-BUCKMINSTERFULLERENE
    AN, YZ
    ANDERSON, JL
    RUBIN, Y
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (18) : 4799 - 4801
  • [2] HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHIC SEPARATION OF FULLERENE MIXTURES USING A NOVEL STATIONARY-PHASE
    BANKS, MR
    GOSNEY, I
    JONES, AC
    JONES, DS
    LANGRIDGESMITH, PRR
    MCQUILLAN, RJ
    THORBURN, P
    [J]. CHROMATOGRAPHIA, 1993, 35 (9-12) : 631 - 634
  • [3] BIS-FUNCTIONALIZATION OF C-60 VIA THERMAL REARRANGEMENT OF AN ISOLABLE FULLEROAZIRIDINE BEARING A SOLUBILIZING SUPERMESITYL ESTER MOIETY
    BANKS, MR
    CADOGAN, JIG
    GOSNEY, I
    HODGSON, PKG
    LANGRIDGESMITH, PRR
    RANKIN, DWH
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (11) : 1365 - 1366
  • [4] INHIBITION OF THE HIV-1 PROTEASE BY FULLERENE DERIVATIVES - MODEL-BUILDING STUDIES AND EXPERIMENTAL-VERIFICATION
    FRIEDMAN, SH
    DECAMP, DL
    SIJBESMA, RP
    SRDANOV, G
    WUDL, F
    KENYON, GL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) : 6506 - 6509
  • [5] DENDRITIC FULLERENES - A NEW APPROACH TO POLYMER MODIFICATION OF C-60
    HAWKER, CJ
    WOOLEY, KL
    FRECHET, JMJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (08) : 925 - 926
  • [6] THE SYNTHESIS AND CHARACTERIZATION OF A SELF-ASSEMBLING AMPHIPHILIC FULLERENE
    HAWKER, CJ
    SAVILLE, PM
    WHITE, JW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) : 3503 - 3505
  • [7] HIRSCH A, 1993, ANGEW CHEM INT EDIT, V32, P1138, DOI 10.1002/anie.199311381
  • [8] IMPROVED PURIFICATION OF C-60 AND FORMATION OF SIGMA-HOMOAROMATIC AND PI-HOMOAROMATIC METHANO-BRIDGED FULLERENES BY REACTION WITH ALKYL DIAZOACETATES
    ISAACS, L
    WEHRSIG, A
    DIEDERICH, F
    [J]. HELVETICA CHIMICA ACTA, 1993, 76 (03) : 1231 - 1250
  • [9] STRUCTURES AND CHEMISTRY OF METHANOFULLERENES - A VERSATILE ROUTE INTO N-[(METHANOFULLERENE)CARBONYL]-SUBSTITUTED AMINO-ACIDS
    ISAACS, L
    DIEDERICH, F
    [J]. HELVETICA CHIMICA ACTA, 1993, 76 (07) : 2454 - 2464
  • [10] FULLERENE AZIRIDINE - FACILE SYNTHESIS AND SPECTRAL CHARACTERIZATION OF FULLERENE URETHANE, C60NCO2CH2CH3
    ISHIDA, T
    TANAKA, K
    NOGAMI, T
    [J]. CHEMISTRY LETTERS, 1994, (03) : 561 - 562