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Beilstein J. Org. Chem. 2014, 10, 956–968, doi:10.3762/bjoc.10.94
Graphical Abstract
Figure 1: Prototypical open and closed geodesic polyarenes.
Figure 2: Planar vs pyramidalized π-system.
Figure 3: Selected examples of geodesic polyarenes synthesized by FVP.
Scheme 1: Covalent functionalization of fullerene C60 by the Bingel–Hirsch reaction and the Prato reaction.
Scheme 2: Fullerene-type chemistry at interior carbon atoms of corannulene (1) and diindenochrysene (10).
Figure 4: POAV angles of fullerene C60 (2), corannulene (1), and diindenochrysene (10).
Scheme 3: Synthesis of circumtrindene (6) by FVP.
Scheme 4: Synthetic route to 3,9,15-trichlorodecacyclene (12).
Figure 5: POAV angle and bond lengths of circumtrindene.
Scheme 5: Bingel–Hirsch reaction of circumtrindene (6).
Scheme 6: Proposed mechanism for the Bingel–Hirsch reaction of circumtrindene (6).
Scheme 7: Prato reaction of circumtrindene (6).
Figure 6: LUMO orbital map of circumtrindene (B3LYP/6-31G*). The darkest blue areas correspond to the regions...
Figure 7: Electrostatic potentials on the surfaces of circumtrindene (B3LPY/6-31G*).
Figure 8: Monoindeno- (25), diindeno- (26), and triindenocircumtrindene (27).
Figure 9: Two different types of rim carbon atoms on circumtrindene.
Scheme 8: Site-selective peripheral monobromination of circumtrindene.
Scheme 9: Suzuki coupling and ring-closing reactions toward indenocircumtrindene (25).
Scheme 10: Suzuki coupling to prepare compound 30.
Figure 10: Chemical shifts of ortho-methyl groups in 30 and 31.