Organic chemistry of C sub 60 (Buckminsterfullerene): Chromatography and osmylation

The efficient macroscopic preparation of C{sub 60} by the contact-arc vaporization of graphite rods has recently brought this enchanting molecule from the realm of molecular beam experiments into that of synthetic organic chemistry. The authors are interested in selectively adding functional groups to C{sub 60} in a way that leaves the carbon skeleton intact and allows for further transformation. They report here the chromatographic separation of C{sub 60} and C{sub 70} on a Pirkle column and the osmylation of C{sub 60}. They chose the powerful but selective oxidant osmium tetraoxide for the functionalization of C{sub 60}. The pyridine-accelerated osmylation of polycyclic aromatic hydrocarbons is well known. The experiments establish the heteroatom functionality can be added to C{sub 60} without disrupting the carbon framework. The authors are currently exploring the regiochemistry of the osmylation and converting the glycolates to other organic functional groups in order to manipulate the C{sub 60} framework.