Electroreductive transformation of [60]fullerosultones into fullerosulfonic acids

J Org Chem. 2013 Jul 19;78(14):7093-9. doi: 10.1021/jo400920f. Epub 2013 Jul 8.

Abstract

Novel C60 derivatives of a singly bonded dimer and a 1,4-adduct bearing a sulfonic acid functionality have been prepared via the electroreductive transformation of a [60]fullerosultone. It has been shown that the reaction of the in situ formed dianion with benzyl bromide is initiated by a ring-opening of the [60]fullerosultone via the C60-O bond cleavage upon receiving one electron. The [60]fullerosultone dianion is electrooxidized at 0.40 V to afford the singly bonded dimer species, which can be further electrooxidized at 1.30 V to restore the starting material [60]fullerosultone. The reaction mechanism is studied with the cyclic voltammetry and vis-NIR spectroscopy.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzenesulfonates / chemistry*
  • Electrochemical Techniques*
  • Fullerenes / chemistry*
  • Molecular Structure
  • Oxidation-Reduction

Substances

  • Benzenesulfonates
  • Fullerenes