Formation of fulleroids as major products and application of solid state reaction in the functionalization of [60]fullerene by aromatic diazoketones

The reactions of various aromatic diazoketones with [60]fullerene were investigated in solution (o-dichlorobenzene) or in the solid-state. Under all the conditions examined, the fulleroid with the methine proton located over a six-membered ring was obtained as a major product along with a slight amount of the other fulleroid diastereoisomer and methanofullerene. Solid-state reactions considerably enhanced the reaction efficiency with minor effects on the selectivity. The thermal isomerization and photoisomerization from fulleroids into methanofullerene were relatively slow, almost independent of substituents under the conditions examined.