Nucleophilic Addition to Fullerenes

Nucleophilic addition of organozinc reagents is crucial step in Reformatsky reaction which was employed for fullerene derivatization. Ethylbromoacetate reagent (5 equiv.) in conjunction with zinc dust (20 equiv.) reacts with fullerene to obtain product 48 in high yield. In this process, known cyclopropane molecule 49 was formed as a side product, as well as two products unknown in the literature, 50 and 51 (Scheme 7.14) [26]. Formation of these products is rationalized by mechanism which starts with formation of organozinc reagent, which is followed by nucleophilic addition to fullerene. 

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