Stepwise synthesis of fullerene cyclopentadienide R5C60- and indenide R3C60-.: An approach to fully unsymmetrically substituted derivatives

被引:45
作者
Sawamura, M [1 ]
Toganoh, M [1 ]
Suzuki, K [1 ]
Hirai, A [1 ]
Iikura, H [1 ]
Nakamura, E [1 ]
机构
[1] Univ Tokyo, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan
关键词
D O I
10.1021/ol005993k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Fullerene cyclopentadienide (PhCH2)(2)Ph3C60- and indenide (PhCH2)(2)PhC60-, each bearing two different organic groups, were efficiently synthesized through regioselective reactions of 1,4-(PhCH2)(2)C-60 with an organocopper reagent (PhMgBr/CuBr . SMe2) or a Grignard reagent (PhMgBr) followed by deprotonation with (KOBu)-Bu-t.
引用
收藏
页码:1919 / 1921
页数:3
相关论文
共 14 条
[1]   SYNTHESIS, CHEMISTRY, AND PROPERTIES OF A MONOALKYLATED BUCKMINSTERFULLERENE DERIVATIVE, T-BUC-60 ANION [J].
FAGAN, PJ ;
KRUSIC, PJ ;
EVANS, DH ;
LERKE, SA ;
JOHNSTON, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (24) :9697-9699
[2]   Formation of C60 adducts with two different alkyl groups via combination of electron transfer and SN2 reactions [J].
Fukuzumi, S ;
Suenobu, T ;
Hirasaka, T ;
Arakawa, R ;
Kadish, KM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (36) :9220-9227
[3]  
Hehre W. J., 1986, Ab initio molecular orbital theory
[4]   SYNTHESIS OF ISOMERICALLY PURE ORGANODIHYDROFULLERENES [J].
HIRSCH, A ;
GROSSER, T ;
SKIEBE, A ;
SOI, A .
CHEMISCHE BERICHTE-RECUEIL, 1993, 126 (04) :1061-1067
[5]   REGIOSPECIFIC COORDINATION OF TERT-BUTYLFULLERIDE ION AND 1,4-DICYCLOPROPYLTROPYLIUM ION - SYNTHESIS OF A DIALKYLDIHYDROFULLERENE HAVING A HETEROLYTICALLY DISSOCIATIVE CARBON-CARBON SIGMA-BOND [J].
KITAGAWA, T ;
TANAKA, T ;
TAKATA, Y ;
TAKEUCHI, K ;
KOMATSU, K .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (06) :1490-1491
[6]   Introduction of two benzyl groups to C-60 by using the Collman reagent [J].
Miki, S ;
Kitao, M ;
Fukunishi, K .
TETRAHEDRON LETTERS, 1996, 37 (12) :2049-2052
[7]   Synthesis, X-ray structure, and properties of the first tetrakisadduct of fullerene C-60 having a fulvene-type pi-system on the spherical surface [J].
Murata, Y ;
Shiro, M ;
Komatsu, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (34) :8117-8118
[8]   SILYLMETHYLATIONS OF C-60 WITH GRIGNARD-REAGENTS - SELECTIVE SYNTHESIS OF HC60CH2SIME2Y AND C60(CH2SIME2Y)2 WITH SELECTION OF SOLVENTS [J].
NAGASHIMA, H ;
TERASAKI, H ;
KIMURA, E ;
NAKAJIMA, K ;
ITOH, K .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (06) :1246-1248
[9]   The first pentahaptofullerene metal complexes [J].
Sawamura, M ;
Iikura, H ;
Nakamura, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (50) :12850-12851
[10]   Synthesis of π-indenyl-type fullerene ligand and its metal complexes via quantitative trisarylation of C70 [J].
Sawamura, M ;
Iikura, H ;
Hirai, A ;
Nakamura, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (32) :8285-8286