Synthesis Of Pyrrolidinofullerenes Via Single Electron Transfer Reaction Of Aryldienamines With C-60

Variously aryl-substituted pyrrolidinofullerenes were synthesized via a single electron transfer (SET) reaction of diaryldienamines with C-60 and the following consecutive 1,6-hydrogen shift and the [3 + 2] cycloaddition of the generated radical ion pair. The LUMO levels of pyrrolidinofullerenes were ca. 0.1 eV higher than C-60, consequently suppressing the bisadduct formation. The phenyl-substituted pyrrolidinofullerene 2a representatively exhibited the protic acid-catalyzed intramolecular Friedel Crafts cyclization and the DDQ induced oxidative reversion into C-60.