Unexpected De-Arylation of a Pentaaryl Fullerene

Simon Clavaguera (1) , Yves Rubin (1)

1 Department of Chemistry and Biochemistry

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.

Domains: Organic chemistry

Simon Clavaguera, Yves Rubin. Unexpected De-Arylation of a Pentaaryl Fullerene. Organic Letters, 2009, 11 (6), pp.1389-1391. ⟨10.1021/ol900224w⟩. ⟨cea-01344098⟩