Bisaziridine Tetracarboxylates as Building Blocks in the Stereoselective Synthesis of C60-Fullerene Diads and Dumbbell-like Bis-C60-fullerene Triads.

The synthesis of alkoxycarbonyl-substituted bisa-ziridines with the two aziridine units connected by conjugated p-phenylene, partly conjugated 1,1'-biphenyl-4,4'diyl, and non-conjugated 4,4'-metriylenediphenyI linkers was developed. The reaction of azomethine ylides derived from the bisaziridines with fullerene C60 was optimized and used for the stereoselective preparation of both the monoadducts (C60-linker-aziridine dicarboxylate), and the dumbbell bisadducts (C60-linker-C60). The reasons for the observed selectivity of the azomethine ylide formation and cydoaddition were theoretically studied at the DFT B3LYP/6-31G(d) level or at the ON1OM B3LYP/631G(d):B3LYP/STO-3G level for fullerene-containing molecules. [ABSTRACT FROM AUTHOR]