ORGN 530 |
| The discovery of the fullerenes has led to a renewed interest in the synthesis of novel aromatic compounds, particularly nonplanar aromatic compounds that represent a portion of C60. Current syntheses of buckybowls have relied on pyrolytic techniques or intramolecular coupling reactions involving transition metals. Most traditional routes to such curved polycyclic aromatic compounds fail because of the large amount of strain introduced and/or unfavorable geometric constraints. We will discuss a means of overcoming these limitations using a ring contraction reaction to introduce curvature into accessible flat polycyclic aromatics precursors. The Wolff rearrangement is ideally suited for this purpose since the expulsion of nitrogen helps offset the strain introduced in forming the fullerene substructures. We will discuss molecular modeling studies that demonstrate the feasibility of this approach as well as synthetic efforts to produce a number of buckybowls including substructures of C60 such as corannulene (1) and sumanene (2), as well as substructures of higher fullerenes such as dicylopentaperylene (3).
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Heterocycles, Aromatics, Metal-Mediated Reactions and Syntheses, Materials, Devices, and Switches
8:00 PM-10:00 PM, Wednesday, 29 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster
Division of Organic Chemistry |
