Synthesis of Imino[60]fullerenes Using Nitriles and Trimethylsilylmethyl Triflate

The synthesis of a new class of fullerene derivatives, 1-imino-4-silylmethyl[60]fullerene derivatives, is described. The anion (C₆₀R¹⁻) of an alkyl- or aryl-adduct of [60]fullerene, C₆₀R¹H (R¹ = CH₂SiMe₃, CH₂SiMe₂Ph, C₆H₄−OMe-4, C₆H₄−NMe₂-4, C₆H₄−CF₃-4 and C₆H₄−OMe-2), was allowed to react with a nitrilium salt [R²CNCH₂SiMe₃][OTf] (Tf = SO₂CF₃) that was generated in situ by the reaction of Me₃SiCH₂OTf and a nitrile solvent R¹CN (R² = Ph and Me). The desired imino[60]fullerene derivative C₆₀(R¹) [C(=NCH₂SiMe₃)R²] was produced in a yield up to 80%. The structure of the product with R¹ = C₆H₄−OMe-4 and R² = Ph was determined by single-crystal X-ray analysis.