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Unexpected De-Arylation of a Pentaaryl Fullerene

Abstract : A triphenylamine-derived pentaaryl fullerene undergoes an unusual oxidative dearylation under basic conditions to give tetraarylated epoxy fullerene in high yield. The structure of the product was confirmed by single crystal X-ray diffraction. A mechanism is proposed to account for the loss of the addend and the subsequent formation of the epoxide group.
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Simon Clavaguera, Yves Rubin. Unexpected De-Arylation of a Pentaaryl Fullerene. Organic Letters, American Chemical Society, 2009, 11 (6), pp.1389-1391. ⟨10.1021/ol900224w⟩. ⟨cea-01344098⟩

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