C70Ph8 spontaneously oxidises in air to form a bis-lactone C70Ph8O4, having an eleven-membered hole in the fullerene cage; the reaction is believed to proceed via insertion of oxygen into 5,6 bonds followed by oxidative cleavage of the adjacent double bond, a process which has a precedent in the spontaneous oxidation of vinyl ethers to esters.
P. R. Birkett, A. G. Avent, A. D. Darwish, H. W. Kroto, R. Taylor and D. R. M. Walton, J. Chem. Soc., Chem. Commun., 1995, 1869 DOI: 10.1039/C39950001869
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