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Science 26 March 1993:
Vol. 259. no. 5103, pp. 1885 - 1887
DOI: 10.1126/science.259.5103.1885
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Articles

C60H2: Synthesis of the Simplest C60 Hydrocarbon Derivative

Craig C. Henderson 1 and Paul A. Cahill 1

1 Department 1811, Sandia National Laboratories, Albuquerque, NM 87185

The reaction of C60 with BH3: tetrahydrofuran in toluene followed by hydrolysis yielded C60H2. This product was separated by high-performance liquid chromatography and characterized as the addition product of H2 to a 6,6-ring fusion (1alb isomer). The 1H nuclear magnetic resonance (NMR) spectrum of the product remained a sharp singlet between –80° and +100°C, which suggests a static structure on the NMR time scale. Hydrolysis of the proposed borane addition product with acetic acid-d1 or D2O yielded C60HD, and its 3JHD coupling constant is consistent with vicinal addition. The observation of a single C60H2 isomer is in complete agreement with earlier calculations that indicated that at most 2 of the 23 possible isomers of C60 would be observable at equilibrium at room temperature. These results suggest that organoborane chemistry may be applied to further functionalization of fullerenes.

Submitted on December 21, 1992
Accepted on February 11, 1993


THIS ARTICLE HAS BEEN CITED BY OTHER ARTICLES:
Taming Superacids: Stabilization of the Fullerene Cations HC60+ and C60{middle dot}+.
C. A. Reed, K.-C. Kim, R. D. Bolskar, and L. J. Mueller (2000)
Science 289, 101-104
   Abstract »    Full Text »
Synthesis, Isolation, and Equilibration of 1,9- and 7,8-C70H2.
C. C. Henderson, C. M. Rohifing, K. T. Gillen, and P. A. Cahill (1994)
Science 264, 397-399
   Abstract »    PDF »
Chemistry of the Fullerenes: The Manifestation of Strain in a Class of Continuous Aromatic Molecules.
R. C. Haddon (1993)
Science 261, 1545-1550
   Abstract »    PDF »


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