C59N+:: A key intermediate in azaheterofullerene chemistry

被引:44
作者
Hauke, F [1 ]
Hirsch, A [1 ]
机构
[1] Inst Organ Chem, D-91054 Erlangen, Germany
关键词
fullerenes; azaheterofullerenes; Mannich reaction; enols;
D O I
10.1016/S0040-4020(01)00235-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The thermal treatment of the azaheterofullerene dimer (C59N)(2) in the presence of oxygen and a nucleophilic trapping reagent leads to the facile and selective formation of a variety of monomeric adducts C59NR involving electronic rich aromatics, carbonyl compounds, alcohols and olefins as terminating addend. These investigations within the field of synthetic heterofullerene chemistry imply the presence of C59N1 as an important key intermediate. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3697 / 3708
页数:12
相关论文
共 8 条
[1]   Synthesis of C-59(CHPh(2))N from (C59N)(2) and C59HN. The first derivatization of C59N [J].
BellaviaLund, C ;
Gonzalez, R ;
Hummelen, JC ;
Hicks, RG ;
Sastre, A ;
Wudl, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (12) :2946-2947
[2]   Fullerene carbon resonance assignments through N-15-C-13 coupling constants and location of the sp(3) carbon atoms of (C59N)(2) [J].
BellaviaLund, C ;
KeshavarzK, M ;
Collins, T ;
Wudl, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (34) :8101-8102
[3]   Mannich functionalization of C59N [J].
Hauke, F ;
Hirsch, A .
CHEMICAL COMMUNICATIONS, 1999, (21) :2199-2200
[4]   ISOLATION OF THE HETEROFULLERENE C59N AS ITS DIMER (C59N)(2) [J].
HUMMELEN, JC ;
KNIGHT, B ;
PAVLOVICH, J ;
GONZALEZ, R ;
WUDL, F .
SCIENCE, 1995, 269 (5230) :1554-1556
[5]  
Keshavarz M., 1996, NATURE, V383, P147
[6]   Facile synthesis of arylated heterofullerenes ArC59N [J].
Nuber, B ;
Hirsch, A .
CHEMICAL COMMUNICATIONS, 1998, (03) :405-406
[7]   A new route to nitrogen heterofullerenes and the first synthesis of (C69N)(2) [J].
Nuber, B ;
Hirsch, A .
CHEMICAL COMMUNICATIONS, 1996, (12) :1421-1422
[8]  
NUBER B, 1998, UNPUB