Chemical Modification of Endohedral Metallofullerene La@C82 with 3-chloro-3-phenyldiazirine

The photochemical reaction of an endohedral metalofullerene La@C82 with 3-chloro-3-phenydiazirine (3) affords the monoadduct as a phenylchlorocarbene (:CClPh) derivative. Spectroscopic analyses of UV-vis-near infrared and electron spin resonance and the theoretical calculations reveal that this monoadduct is a pair of stereoisomers with carbene substituents, and the carbene addition occurs regioselectively to the carbons having a high charge density and a high local strain of the C82 cage.