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 (C(60)R(1-)) of an alkyl- or aryl-adduct of [60]fullerene, C(60)R(1)H (R(1) = CH(2)SiMe(3), CH(2)SiMe(2)Ph, C(6)H(4)-OMe-4, C(6)H(4)-NMe(2)-4, C(6)H(4)-CF(3)-4 and C(6)H(4)-OMe-2), was allowed to react with a nitrilium salt [R(2)CNCH(2)SiMe(3)][OTf] (Tf = SO(2)CF(3)) that was generated in situ by the reaction of Me(3)SiCH(2)OTf and a nitrile solvent R(1)CN (R(2) = Ph and Me). The desired imino[60]fullerene derivative C(60)(R(1)) [C(=NCH(2)SiMe(3))R(2)] was produced in a yield up to 80%. The structure of the product with R(1) = C(6)H(4)-OMe-4 and R(2) = Ph was determined by single-crystal X-ray analysis.
Matsuo
Keiko
K
Department of Chemistry, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Matsuo
Yutaka
Y
Iwashita
Akihiko
A
Nakamura
Eiichi
E