Regioselective Synthesis of 1,4-Di(organo)fullerenes through DMF-assisted Monoaddition of Silylmethyl Grignard Reagents and Subsequent Alkylation Reaction
datasetposted on 19.11.2008, 00:00 by Yutaka Matsuo, Akihiko Iwashita, Yoko Abe, Chang-Zhi Li, Keiko Matsuo, Masahiko Hashiguchi, Eiichi Nakamura
Monoaddition of Grignard reagents, in particular tri(organo)silylmethylmagnesium chlorides, to fullerene took place smoothly in the presence of dimethylformamide to produce (organo)(hydro)fullerenes, C60R1H, in good yield (up to 93% isolated yield). The hydrofullerene was then deprotonated to generate the corresponding anion, C60R−, which was then alkylated to obtain 58π-electron di(organo)fullerenes, C60R1R2, in good to high yield (up to 93% overall yield). The two-step methodology provides a wide variety of 1,4-di(organo) fullerenes bearing the same or different organic addends on the  fullerene core. By changing the addends, one can control the chemical and physical properties of the compounds at the molecular and bulk levels.