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The Orthogonal ( e , e , e )‐Tris‐Adduct of 9,10‐Dimethylanthracene with C 60 ‐Fullerene: A Hidden Cornerstone of Fullerene Chemistry. Preliminary Communication
Author(s) -
DuarteRuiz Alvaro,
Wurst Klaus,
Kräutler Bernhard
Publication year - 2008
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200890152
Subject(s) - adduct , chemistry , tris , fullerene , cycloaddition , monoclinic crystal system , crystal structure , crystallography , medicinal chemistry , organic chemistry , catalysis , biochemistry
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.