CYCLOADDITIONS .48. ADDITION OF PHOTOCHEMICALLY GENERATED ACYLNITRENES TO C-60 - SYNTHESIS OF FULLEROAZIRIDINES AND THERMAL REARRANGEMENT TO FULLEROOXAZOLES

被引：48
作者：
AVERDUNG, J
MATTAY, J
JACOBI, D
ABRAHAM, W
机构：
[1] UNIV MUNSTER,INST ORGAN CHEM,D-48149 MUNSTER,GERMANY
[2] HUMBOLDT UNIV BERLIN,INST CHEM,D-10115 BERLIN,GERMANY
来源：
TETRAHEDRON | 1995年 / 51卷 / 09期
关键词：
60]FULLERENE; AZIRIDINE; OXAZOLE; NITRENE; AZIDE; PHOTOREACTION;
D O I：
10.1016/0040-4020(95)00013-X
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of C-60 to acylnitrenes 2, generated by photolysis of aroylazides 1 in dichloromethane, creates the stable fulleroaziridine derivatives 3a, 3b, 3c, and 3d. The rearrangement of the fulleroaziridines 3 by boiling in tetrachloroethane leads to the formation of the corresponding fullerooxazoles 4a, 4b, 4c, and 4d. The formation of a fullerooxazole 4b was also observed by irradiation of C-60 and 1b in benzene.
引用
收藏
页码：2543 / 2552
页数：10
相关论文
共 23 条
  • [1] ORGANIC-CHEMICAL DERIVATION OF FULLERENES .4. ADDUCT OF C70 AT THE EQUATORIAL BELT - PHOTOCHEMICAL CYCLOADDITION WITH DISILIRANE
    AKASAKA, T
    MITSUHIDA, E
    ANDO, W
    KOBAYASHI, K
    NAGASE, S
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (06) : 2627 - 2628
  • [2] PHOTOCHEMICAL [2+3] CYCLOADDITION OF C-60 WITH DISILIRANES
    AKASAKA, T
    ANDO, W
    KOBAYASHI, K
    NAGASE, S
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) : 10366 - 10367
  • [3] 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
  • [4] [Anonymous], 1993, ANGEW CHEM, V105, P1189
  • [5] PHOTOREACTIONS WITH C60-FULLERENE - [3+2] PHOTOCYCLOADDITION OF 2,3-DIPHENYL-2H-AZIRINE
    AVERDUNG, J
    ALBRECHT, E
    LAUTERWEIN, J
    LUFTMANN, H
    MATTAY, J
    MOHN, H
    MULLER, WH
    TERMEER, HU
    [J]. CHEMISCHE BERICHTE, 1994, 127 (04) : 787 - 789
  • [6] CYCLOADDITIONS .47. CYCLOADDITION OF 1,8-DEHYDRONAPHTHALENE TO [60]FULLERENE IN BENZENE SOLUTION - A NEW FUNCTIONALIZATION OF C-60 BY IN-SITU GENERATED 6B,1OA-DIHYDROFLUORANTHENE
    AVERDUNG, J
    MATTAY, J
    [J]. TETRAHEDRON LETTERS, 1994, 35 (36) : 6661 - 6664
  • [7] 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
  • [8] Further studies on a molecular rearrangement induced by ultrasonic waves
    Barrett, EW
    Porter, CW
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1941, 63 : 3434 - 3435
  • [9] PHOTOCHEMISTRY OF ACYLAZIDES .8. DO ACYLNITRENES REACT LIKE 1,3-DIPOLES
    BUCK, K
    JACOBI, D
    PLOGERT, Y
    ABRAHAM, W
    [J]. JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1994, 336 (08): : 678 - 685
  • [10] SYNTHESIS AND CHARACTERIZATION OF (C60)O, THE 1ST FULLERENE EPOXIDE
    CREEGAN, KM
    ROBBINS, JL
    ROBBINS, WK
    MILLAR, JM
    SHERWOOD, RD
    TINDALL, PJ
    COX, DM
    SMITH, AB
    MCCAULEY, JP
    JONES, DR
    GALLAGHER, RT
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (03) : 1103 - 1105
123