Open geodesic polyarenes constitute a novel family of hydrocarbons that hold just as much fascination as their closed geodesic cousins, the fullerenes. Circumtrinedene (1 ) is the largest member of this family and was first prepared in our laboratories. Cyclopropanation of circumtrindene proceeds with bromomalonate and DBU to afford 2  in good yield. This represents the first example of a Bingel reaction of a non-fullerene polycyclic hydrocarbon. Unique structural/electronic properties of 1  as well as its reactivity toward metal complexation will also be presented.

Synthesis and reactions of a highly-strained open geodesic polyarene

243rd National Meeting (2012)

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