C 60 H 2 : Synthesis of the Simplest C 60 Hydrocarbon Derivative

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Abstract
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.