Spontaneous oxidation of C60Ph5X (X = H, Cl) to a benzo[b]furanyl[60]fullerene

On exposure to air, both C 60 Ph 5 H and C 60 Ph 5 Cl spontaneously oxidise with elimination of the hydrogen or chlorine attached to the cage and the ortho hydrogen of the adjacent phenyl group, giving a benzo[b]furanyl[60]fullerene; a second oxygen is located in the pentagon that is surrounded by phenyl groups.