Ozonolysis of [60]fullerene (&) generates a mixture of the oxidized products having ketone, ester, and epoxide functionalities; an intermediate in this reaction can also transfer an oxygen to aromatic compounds to give normal and NIH-shifted phenols.

We have explored several cycloaddition reactions as a general approach for preparing fullerene derivatives. In view of their electron-deficient nature, they are expected to participate as dienophiles rather than dienes in cycloadditions. This behavior is exemplified in their reactions with sulfur trioxide, diphenylisobenzofuran, and the nitrone from cyclohexanone and N-methyl-hydroxylamine. Fullerenes also formed adducts with maleic anhydride, although in this case the nature of the adduct is not clear. While changes in physical properties such as solubility or IR spectra clearly indicated formation of adducts, mass spectral analysis of diese and many other fullerene derivatives often showed ions due to fullerenes; thus confirmatory evidence for the derivatives was not available from mass spectrometry.

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