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Nucleophilic Additions

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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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