C60F14OFPh3, a fluoroxy derivative of C60F15Ph3; evidence for the presence of ‘missing’ fluorine through restricted rotation of a phenyl group

From the reaction of C60F18 with benzene in the presence of SbCl5 we have isolated a compound of 1252 amu indicated to be C60F14OFPh3, a fluoroxyfullerene. Temperature-variable 1H NMR shows that one phenyl group suffers restricted rotation on cooling to 218 K, attributed to the presence of the OF group which, as in the case of the recently characterised C60F17OF, fails to give a signal for this group in the 19F NMR. We have isolated also, C60F14O2FPh3 (1268 amu) a mixture of oxahomo derivatives of C60F14OFPh3 arising from oxygen insertion into FCCF bonds. Theoretical calculations for C60F14OFPh3 indicate that the phenyl group nearest to the OF group is twisted out of the plane containing the other two.