Fullerene-like chemistry at the interior carbon atoms of an alkene-centered C26H12 geodesic polyarene.

摘要: The title compound (1) undergoes 1,2-addition reactions of both electrophilic and nucleophilic reagents preferentially at the “interior” carbon atoms central 6:6-bond to give fullerene-type adducts 2, 3, 4, 5. Such fullerene-like chemistry is unprecedented for a topologically 2-dimensional polycyclic aromatic hydrocarbon qualifies this geodesic polyarene as “bridge” between old flat world hydrocarbons (PAHs) new round fullerenes. relief pyramidalization strain, in addition fullerenes, presumably contributes atypical mode reactivity seen 1. Molecular orbital calculations, however, reveal features nonalternant π system 1 that may also play an important role. Thus, be driven by two or more factors, relative importances which are difficult discern.