Optically active carbon: kinetic resolution of c76 by asymmetric osmylation.
The chiral fullerene C(76) was kinetically resolved by asymmetric osmylation providing an example of an optically active allotrope of a pure element. C(76) recovered from the treatment of racemic C(76) with OsO(4) and a chiral alkaloid ligand, showed a specific rotation [alpha](D) of -4000 degrees (> 97 percent enantiomeric excess) and a circular dichroism spectrum corresponding to the ultraviolet spectrum. Regenerated C(76) formed by reducing the asymmetrically osmylated C(76) with SnCl(2) was enriched in the opposite enantiomer. Analysis of the local curvature of the C(76) molecule indicated that OsO(4) should selectively add to 2 of the 30 types of bonds in C(76). This regioselectivity was supported chromatographically and interpreted in terms of the kinetic resolution.
Hawkins
J M
JM
Meyer
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