Soccer goes BOXing: Synthetic access to novel [6:0] hexakis[(bisoxazolinyl)methano]fullerenes

Abstract

The syntheses of [6:0] hexakis[(bisoxazolinyl)methano]fullerenes are presented. Two derivatives could be directly obtained using conditions developed by the Sun group. For the remaining products, a two stage protocol had to be developed. All compounds we obtained in synthetically useful scales and were purified via column chromatography with standard achiral phase. These new fullerene adducts bear six metal-chelation sites which are aligned in the three orthogonal space directions and are disposed on a completely rigid scaffold. First experiments indicate that the generation of six-fold metal-complexes is possible with these structures. This makes them very appealing as ligands in asymmetric catalysis and as building blocks in higher supra-molecular assemblies.