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Benzyne was found to add to C60 in good yield to give C60(C6H4)n (n=1−4). Typical Diels-Alder dienes were also found to add to C60 under thermally mild conditions. Adducts of C60 with 2,3-dimethylbutadiene, cyclopentadiene, hexa-chlorocyclopentadiene, 1,3-diphenylisobenzofuran, and anthracene were obtained. Further reactions of these products such as elimination and autooxidation reactions were investigated. Addition reaction of dichlorocarbene to C60 gave C61Cl2. Oxidation of C60 with m-chloroperbenzoic acid gave C60On(n=1, 2). All of the products were isolated by means of HPLC and characterized by mass spectroscopy.
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Nogami et al. (1993) studied this question.
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