Regioselective Preparation of Fullerene Bis?adducts from Cleavable Macrocyclic Bis?malonates

A series of macrocyclic bis-malonates incorporating either di-tert-butylsilylene or tetra-iso-propyldisiloxane subunits have been prepared and used for the regioselective bis-functionalization [60]fullerene by double Bingel cyclopropanations. By systematically changing length rigidity spacer units linking malonate moieties to silylated protecting groups, fullerene bis-adducts with different addition patterns obtained. Finally, bridging groups cleaved afford corresponding acyclic bearing four alcohol functions.