Circumtrindene: A geodesic dome of molecular dimensions. Rational synthesis of 60% of C-60

The title compound (1), which had previously been available in only 0.2% yi eld by flash vacuum pyrolysis (FVP) of decacyclene (2) at 1200-1300 degrees C, has now been prepared in 25-27% yield by FVP of 3,9,15-trichlorodecacyc lene (5b) at 1100 degrees C. The propeller-shape 5b was synthesized by aldo l cyclotrimerization of 8-chloro-1(2H)-acenaphthylenone (8b), which, in tur n, was prepared by a simple four-step synthesis from 2-chloronaphthalene, T he synthetic strategy demonstrated here, which has improved the yield of ci rcumtrindene (1) by more than 2 orders of magnitude, should be applicable t o the rational synthesis of larger geodesic polyarenes, both open (bowls, b askets, tubes, etc.) and closed (fullerenes).