ORGN 118 |
| Shih-Ching Chuang, Saeed I. Khan, and Yves Rubin. Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Ave, Los Angeles, CA 90095-1569 |
| The synthesis of [60]fullerene derivatives with openings in the carbon framework and the subsequent insertion of atoms into the C60 core is of great interest because of the anticipated physical properties these compounds should have. The approach used to open C60 is proposed to follow a [2+2+2] ring-opening mechanism. Two candidate molecules were designed and synthesized. Bis-isobenzofuran-tris-Bingel adducts 1 and 2 can be provided with radical generating centers for addition to the last C=C bond of the functionalized 6-membered ring. Without the Bingel functionalization, the bisisobenzofuran adducts show practically no HOMO or LUMO coefficients at the last double bond to be saturated, which can explain why this system has failed opening attempts. However, the current modified trans-4, trans-4, trans-4 Bingel trisadduct offers a good chance to saturate the last double bond because of the strong HOMO/LUMO coefficients it now displays via modification of the cage electronic structure. Results from a computational search of Bingel addition sites on the bisisobenzofuran system has resulted in the pursuit of isobenzofuran adducts 1 and 2 having the strong HOMO/LUMO coefficients. Characterization of the Bingel addition products on the cis-1 bisisobenzofuran adduct will be presented. In a more basic study, the kinetics of isobenzofuran additions to C60 and the thermodynamic stability of the mono and cis-1 bisisobenzofuran adducts have been investigated by NMR and TGA. |
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New Reactions and Methodology, Metal-Mediated Reactions, Heterocycles and Aromatics
8:00 PM-10:00 PM, Sunday, March 28, 2004 Anaheim Convention Center -- Hall A, Poster
Division of Organic Chemistry |
