Stereoselective synthesis of cis- and trans-2′,5′-disubstituted N-arylpyrrolo[3′,4′:1,9](C60-I h )[5,6]fullerenes by the 1,3-dipolar cycloaddition of azomethine ylides from dialkyl aziridinedicarboxylates to fullerene C60

被引：16
|
作者：
Konev, A. S. [1 ]
Mitichkina, A. A. [1 ]
Khlebnikov, A. F. [1 ]
Frauendorf, H. [2 ]
机构：
[1] St Petersburg State Univ, Dept Chem, St Petersburg 198504, Russia
[2] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
来源：
RUSSIAN CHEMICAL BULLETIN | 2012年 / 61卷 / 04期
基金：
俄罗斯基础研究基金会;
关键词：
pyrrolofullerenes; aziridines; azomethine ylides; POT 3-COMPONENT REACTION; BUILDING-BLOCKS; AMINO-ACID; DERIVATIVES; FULLEROPYRROLIDINES; AZIRIDINES; SYSTEMS; FUNCTIONALIZATION; ANTIBACTERIAL; NANOMATERIALS;
D O I：
10.1007/s11172-012-0121-7
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A stereoselective method for the synthesis of 2',5'-disubstituted N-arylpyrrolofullerenes from anilines, alkyl glyoxylates, alkyl diazoacetates, and fullerene C-60 was proposed. The key step of the synthesis is the 1,3-dipolar cycloaddition reaction of fullerene with azomethine ylides generated by heating of dialkyl aziridinedicarboxylates. The thermal opening of the aziridine ring to azomethine ylide and the cycloaddition of the latter to C-60 at 100 A degrees C are nearly completely stereoselective: only trans-adducts are formed from cis-aziridines, whereas trans-aziridines give exclusively cis-adducts.
引用
收藏
页码：863 / 870
页数：8
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