Treatment of [60]fullerene with an organocopper reagent converts one of the pentagons of the fullerene into cyclopentadienyl anion through addition of five organic groups on every peripheral carbon atom surrounding the pentagon. Similar treatment of [70]fullerene afforded indenyl anion through regioselective tri-addition of the organic group. These anionic moieties strongly interact with the remainder of the fullerene p-system, and provide unique opportunity for exploration of organometallic chemistry of a new class of metal cyclopentadienides.
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Nakamura et al. (2001) studied this question.
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