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

被引：0
作者：
A. S. Konev
A. A. Mitichkina
A. F. Khlebnikov
H. Frauendorf
机构：
[1] Saint Petersburg State University,Department of Chemistry
[2] Institute of Organic and Biomolecular Chemistry of Georg-August-University,undefined
来源：
Russian Chemical Bulletin | 2012年 / 61卷
关键词：
pyrrolofullerenes; aziridines; azomethine ylides;
D O I：
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中图分类号：
学科分类号：
摘要：
A stereoselective method for the synthesis of 2′,5′-disubstituted N-arylpyrrolofullerenes from anilines, alkyl glyoxylates, alkyl diazoacetates, and fullerene C60 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 C60 at 100 °C are nearly completely stereoselective: only trans-adducts are formed from cis-aziridines, whereas trans-aziridines give exclusively cis-adducts.
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页码：863 / 870
页数：7
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