Unexpected de-arylation of a pentaaryl fullerene.

Org Lett

Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.

Published: March 2009

AI Article Synopsis

  • A triphenylamine-based fullerene was modified under basic conditions, leading to the formation of a tetraarylated epoxy fullerene.
  • The high yield product's structure was verified using single crystal X-ray diffraction.
  • A mechanism explaining the process of dearylation and epoxide formation was suggested.

Article 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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http://dx.doi.org/10.1021/ol900224wDOI Listing

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