American Chemical Society
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Lowering Inversion Barriers of Buckybowls by Benzannelation of the Rim:  Synthesis and Crystal and Molecular Structure of 1,2-Dihydrocyclopenta[b,c]dibenzo[g,m]corannulene

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journal contribution
posted on 2001-10-04, 00:00 authored by Zbigniew Marcinow, Andrzej Sygula, Arkady Ellern, Peter W. Rabideau
The title compound (3) has been synthesized by a non-pyrolytic route providing a 36% isolated yield in the final step. X-ray crystal structure determination shows that 3 crystallizes with one solvating molecule of toluene and exhibits slightly lower curvature than the parent cyclopentacorannulene. DFT calculations predict a substantially lower bowl-to-bowl inversion barrier for 3 than for dihydro-cyclopentacorannulene, and this is confirmed by dynamic 1H NMR experiments.