Geodesic polyarenes with exposed concave surfaces

Abstract

Polycyclic aromatic hydrocarbons (PAHs) in which five-membered rings have been interspersed among the six-membered rings generally display curved π systems that can be either fully closed (fullerenes) or partially open (bowl-shaped fullerene fragments), depending on the number of five-membered rings. Both classes of compounds belong to the larger family we call 'GEODESIC POLYARENES.' Herein, we highlight the utility of high temperature aryl radical cyclizations as a general strategy for constructing strained geodesic polyarenes. We also report the first examples of reactions at the 'interior' carbon atoms of neutral PAHs that are not fullerenes, e.g. carbene additions, 1,3-dipolar cycloadditions, osmylation, nucleophilic addition of MeLi, and electrophilic addition of ⊕CHCl2 and ⊕CCl3. © 1999 IUPAC.