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

Abstract

The reaction of C(60) with BH(3): tetrahydrofuran in toluene followed by hydrolysis yielded C(60)H(2). This product was separated by high-performance liquid chromatography and characterized as the addition product of H(2) to a 6,6-ring fusion (1alb isomer). The (1)H nuclear magnetic resonance (NMR) spectrum of the product remained a sharp singlet between -80 degrees and +100 degrees C, which suggests a static structure on the NMR time scale. Hydrolysis of the proposed borane addition product with acetic acid-d(1) or D(2)O yielded C(60)HD, and its (3)J(HD) coupling constant is consistent with vicinal addition. The observation of a single C(60)H(2) isomer is in complete agreement with earlier calculations that indicated that at most 2 of the 23 possible isomers of C(60) would be observable at equilibrium at room temperature. These results suggest that organoborane chemistry may be applied to further functionalization of fullerenes.