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

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 α- and β-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 ¹ H and ¹³ C{ ¹ H} 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.