Details

Autor(en) / Beteiligte

• Stuparu, Mihaiela
• Lentz, Dieter
• Rüegger, Heinz
• Schlüter, A. Dieter

Titel

Exploring the Chemistry of a Double-Stranded Cycle with the Carbon Skeleton of the Belt Region of the C84 Fullerene

Ist Teil von

• European Journal of Organic Chemistry, 2007, Vol.2007 (1), p.88-100

Ort / Verlag

Weinheim: WILEY-VCH Verlag

Erscheinungsjahr

2007

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Intense scale‐up efforts greatly improved the availability of the known double‐stranded cycle 2 with two bridging ether units. The chemistry of 2 towards Bronsted and Lewis acids could, therefore, be investigated quite comprehensively. It was discovered that the reactivity of 2, whose carbon framework resembles the belt region of the C84 (D2) fullerene, is rather unusual as compared with acyclic model compounds. Whereas the latter could easily be dehydrated to the corresponding planar arenes, the former gave rise to a bouquet of unexpected reactions, which all avoided the aromatization of 2 to its still‐elusive, fully conjugated congener B. Intermediates generated from 2 under acidic conditions attack the solvent (e.g. toluene) to give 4, form bridging lactones to give 11 or close back to starting material 2 (e.g. from 16) rather than dehydrate to more highly conjugated structures on the way to the fully unsaturated target cycle B. The structure of compound 4 was solved by X‐ray diffraction. Through the reactions of 2 with Lewis acids, derivatives 14 and 15 became accessible. They are candidates for future attempts to achieve the desired aromatization under basic conditions or by thermal treatment. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)