Nucleophilic Additions
Nucleophilic additions are possible with C60. The first examples can be found in the addition of organolithium or Grignard compounds, but also the addition of cyanide groups and of hetero-groups containing phosphorous or silicon follow the same route. Nucleophilic additions results in monofunctionalized fullerene and usually occur in a 1,2-addition fashion. As reported by Hirsch, the reaction with nucleophiles starts with the formation of an intermediate NunC60n- that can be later stabilized by the addition of an electrophile (E+) or neutral E-X to give C60(ENu)n, an SNi or internal addition reaction to give methanofulleres and cyclohexenofullerenes, or by oxidation to give C60Nu2.[39] It is to be noticed that, technically, the Bingel-reaction
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