Diastereospecific and Highly Site-Selective Functionalization of C-70 Fullerene by a Reaction with Diethyl N-Arylaziridine-2,3-dicarboxylates

摘要

The diastereospecific and highly site-selective cycloaddition of N-arylazomethine ylides generated in situ from diethyl N-arylaziridine-2,3-dicarboxylates to C-70 fullerene is reported. The reaction provides C-70 fulleropyrrolidines in up to hundreds on a milligram scale as alpha- and beta-adducts in a 4:1 ratio with a controlled stereochemical outcome: cis-aziridines give exclusively trans-adducts, and trans-aziridines give only cis-adducts. The H-1 and C-13{H-1} NMR spectra for different isomeric adducts were recorded and analyzed to identify some characteristic features, which permit an easy identification of isomeric adducts of this type.