Nano surgery of C60: The first synthesis of 1,2,3,4,5,6-hexasubstituted C60, a precursor of open C60?

ORGN 176

Shih Ching Chuang and Yves Rubin. Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095-1569
Open the C60 core with [2+2+2] cycloreversion by saturating three C=C bonds within the same six-membered ring of C60 has inspired us to prepare cis-1 bisisobenzofuran-C60. It has been predicted that formation of 1,2,3,4,5,6-hexasubstituted C60 adduct impossible due to steric hedrance and orbital coefficient concerns. During this course, we have attempted to saturate the third C=C bond by generating reactive centers within side chains. Recently, we succeed in synthesizing 1, structurally evidenced by its spectral data (HMBC). AM1 computational study shows that the heat of formation of the open form (5,6 open) 2 is 33.4 kcal/mol higher than that of adduct 1, which implies heating could equilibrate 1 and 2. Herein, the synthesis of 1,2,3,4,5,6-hexasubstituted C60 1 and its differential scan calorimetry (DSC) result will be presented. This could produce a thermal-controlled reversible open C60 derivative.

 

Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Materials, Molecular Recognition
8:00 PM-10:00 PM, Sunday, August 22, 2004 Pennsylvania Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004