A rigid macrocyclic bis-malonate for the regioselective preparation of trans-1 and trans-3 fullerene bis-adducts

A macrocyclic bis-malonate incorporating two rigid di(phenylethynyl)silane moieties has been prepared and used to functionalize C60 in a double Bingel cyclopropanation. Two regioisomeric bis-adducts have been thus obtained, namely the trans-1 and trans-3 isomers. The formation of these specific isomers is favored by both the size of the starting macrocycle and the minimum of strain in the final products.