The Orthogonal ( e , e , e )‐Tris‐Adduct of 9,10‐Dimethylanthracene with C 60 ‐Fullerene: A Hidden Cornerstone of Fullerene Chemistry. Preliminary Communication

Tris(9′,10′‐dimethyl[9,10]ethanoanthracene[11′,12′: 1,9;11″,12″: 16,17;11′′′,12′′′: 30,31])[5,6]fullerene C 60 , the orthogonal ( e , e , e )‐tris‐adduct of C 60 and 9,10‐dimethylanthracene, was obtained from [4+2]‐cycloaddition ( Diels–Alder reaction) at room temperature. The thermally unstable orange red ( e , e , e )‐tris‐adduct was purified by chromatography and was isolated in the form of red monoclinic crystals. Its C 3 ‐symmetric addition pattern was established spectroscopically. Its structure could be further investigated by single crystal X‐ray diffraction. The ( e , e , e )‐tris‐adduct of C 60 and 9,10‐dimethylanthracene has earlier been suggested as intermediate and reversibly formed critical component in ‘template directed’ addition reactions of C 60 . This previously elusive compound has now been isolated and structurally characterized.