Site-selective covalent functionalization at interior carbon atoms and on the rim of circumtrindene, a C₃₆H₁₂ open geodesic polyarene

• Hee Yeon Cho,
• Ronald B. M. Ansems and
• Lawrence T. Scott

Beilstein J. Org. Chem. 2014, 10, 956–968, doi:10.3762/bjoc.10.94

• reactions and to probe the magnetic environment of the concave/convex space around the hydrocarbon bowl. For both classes of functionalization, computational results are reported to complement the experimental observations. Keywords: Bingel–Hirsch reaction; buckybowl; carbon nanomaterials; cyclopropanation

• unit. Representative synthetic reactions of fullerene C60 (2) include cyclopropanation [29][30], [3 + 2] cycloaddition [31][32], [4 + 2] cycloaddition [33], nucleophilic addition [34], and radical addition reactions [35]. Two of the earliest and most widely used reactions, the Bingel–Hirsch reaction

• [29][30] and the Prato reaction [31][32] are illustrated in Scheme 1. The Bingel–Hirsch reaction affords a cyclopropanated fullerene 7, and the Prato reaction gives a [3 + 2] cycloaddition adduct 8. Concurrent with the development of covalent functionalization, numerous noncovalent functionalization