Unlike the facile addition of aliphatic amines to fullerenes, heteroaromatic compounds with NH group do not react directly with pristine fullerenes. The present work reports the preparation of several cyclopentadienyl type fullerene derivatives with pyrazole and pyrrole addends through replacement reactions of C 60 Cl 6 in the presence of tetrabutylammonium bromide. The method has also been applied for the synthesis of aniline and methoxyamine fullerene cyclopentadienyl type adducts. Radical species were involved in the reaction mechanism.
- nucleophilic aromatic substitution
- substituent effect