Strain-induced carbon-carbon bond cleavage of bowl-shaped sumanenone

This study details a highly effective ring-opening reaction that involves acid-mediated carbon-carbon bond cleavage of the buckybowl, sumanenone. The reaction of the bowl-shaped sumanenone with AcOH and TfOH results in the formation of a planar carboxylic acid. The examination of reactivity in comparison to planar analogues, along with theoretical calculations, suggests that the release of curved strain is a crucial factor for the success of this reaction. This study details a highly effective ring-opening reaction that involves acid-mediated carbon-carbon bond cleavage of the buckybowl, sumanenone.