REACTION OF C-60 WITH DIMETHYLDIOXIRANE - FORMATION OF AN EPOXIDE AND A 1,3-DIOXOLANE DERIVATIVE

被引:187
作者
ELEMES, Y [1 ]
SILVERMAN, SK [1 ]
SHEU, CM [1 ]
KAO, M [1 ]
FOOTE, CS [1 ]
ALVAREZ, MM [1 ]
WHETTEN, RL [1 ]
机构
[1] UNIV CALIF LOS ANGELES,DEPT CHEM & BIOCHEM,LOS ANGELES,CA 90024
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1992年 / 31卷 / 03期
关键词
D O I
10.1002/anie.199203511
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Not an oxygen-bridged annulene (structural type 1) but rather an epoxide (structural type 2) is the product of the reaction of dimethyldioxirane with C60. In a competing reaction, a 1,3-dioxolane (structural type 3) is formed-probably by a diradical mechanism. Cleavage of acetone from 3 leading to 2 was not observed at temperatures up to 110-degrees-C. Compound 3 could provide access to ring-opened fullerenes.
引用
收藏
页码:351 / 353
页数:3
相关论文
共 42 条
  • [1] DIMETHYLDIOXIRANE EPOXIDATION OF ALPHA,BETA-UNSATURATED KETONES, ACIDS AND ESTERS
    ADAM, W
    HADJIARAPOGLOU, L
    NESTLER, B
    [J]. TETRAHEDRON LETTERS, 1990, 31 (03) : 331 - 334
  • [2] DIMETHYLDIOXIRANE EPOXIDATION OF ALKENES BEARING 2 ELECTRON DONATING SUBSTITUENTS
    ADAM, W
    HADJIARAPOGLOU, L
    WANG, XH
    [J]. TETRAHEDRON LETTERS, 1991, 32 (10) : 1295 - 1298
  • [3] EPOXIDATION OF ENOL SILYL ETHERS, PHOSPHATES, ESTERS, AND LACTONES BY DIMETHYLDIOXIRANE
    ADAM, W
    HADJIARAPOGLOU, L
    JAGER, V
    KLICIC, J
    SEIDEL, B
    WANG, XH
    [J]. CHEMISCHE BERICHTE, 1991, 124 (10) : 2361 - 2368
  • [4] EPOXIDATION OF SILYL ENOL ETHERS, PHTHALIDES, AND ENOL ESTERS BY DIMETHYLDIOXIRANE
    ADAM, W
    HADJIARAPOGLOU, L
    WANG, XH
    [J]. TETRAHEDRON LETTERS, 1989, 30 (47) : 6497 - 6500
  • [5] CHARACTERIZATION OF THE SOLUBLE ALL-CARBON MOLECULES C60 AND C70
    AJIE, H
    ALVAREZ, MM
    ANZ, SJ
    BECK, RD
    DIEDERICH, F
    FOSTIROPOULOS, K
    HUFFMAN, DR
    KRATSCHMER, W
    RUBIN, Y
    SCHRIVER, KE
    SENSHARMA, D
    WHETTEN, RL
    [J]. JOURNAL OF PHYSICAL CHEMISTRY, 1990, 94 (24) : 8630 - 8633
  • [6] THE UNUSUAL ELECTRON-SPIN-RESONANCE OF FULLERENE C60.-
    ALLEMAND, PM
    SRDANOV, G
    KOCH, A
    KHEMANI, K
    WUDL, F
    RUBIN, Y
    DIEDERICH, F
    ALVAREZ, MM
    ANZ, SJ
    WHETTEN, RL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (07) : 2780 - 2781
  • [7] 2 DIFFERENT FULLERENES HAVE THE SAME CYCLIC VOLTAMMETRY
    ALLEMAND, PM
    KOCH, A
    WUDL, F
    RUBIN, Y
    DIEDERICH, F
    ALVAREZ, MM
    ANZ, SJ
    WHETTEN, RL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (03) : 1050 - 1051
  • [8] Beckhaus H. D., 1992, ANGEW CHEM, V104, P69
  • [9] THE STABILITY OF BUCKMINSTERFULLERENE (C-60) - EXPERIMENTAL-DETERMINATION OF THE HEAT OF FORMATION
    BECKHAUS, HD
    RUCHARDT, C
    KAO, M
    DIEDERICH, F
    FOOTE, CS
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (01): : 63 - 64
  • [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