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A scalable synthesis of methano[60]fullerene and congeners by the oxidative cyclopropanation reaction of silylmethylfullerene

, : A scalable synthesis of methano[60]fullerene and congeners by the oxidative cyclopropanation reaction of silylmethylfullerene. Journal of the American Chemical Society 133(21): 8086-8089

1,2-Dihydromethano[60]fullerene and its congeners have attracted much interest, but they have been synthesized only in very low yields because of several insurmountable problems. A new three-stage synthesis involving addition of a silylmethylmagnesium chloride to [60]- and [70]fullerene and oxidation of the anionic intermediate with CuCl(2) afforded the methano[60]- and methano[70]fullerenes in 90% and 70% overall yield, respectively. The reaction with 1,4-diorgano[60]fullerene also proceeded smoothly to give a diastereomerically pure 56-π-electron fullerene that has a higher LUMO level than the parent fullerene and gave a higher open-circuit voltage and better power conversion efficiency when fabricated into an organic photovoltaic device.


PMID: 21534625

DOI: 10.1021/ja201267t

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