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

On exposure to air, both C60Ph5H and C60Ph5Cl 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