Selective Addition of Aniline to a Cage-opened Diketo Anhydride Derivative of C60

Abstract

Abstract The nucleophilic addition of aniline was examined using a diketo cage-opened C60 derivative possessing an acid anhydride moiety. While the imination occurred at the 1,4-dicarbonyl moiety, the aminalization dominantly proceeded on the anhydride moiety in the presence of zinc(II). The thus formed aminal was thermally converted into acid anhydride while it could be transformed into corresponding isoimide by the use of acid catalyst. The introduced aniline moiety significantly perturbed the orifice size so that the insertion/escape dynamics of a water molecule were substantially restricted.