Synthesis of [60]fullerene derivatives with an octahedral addition pattern

Lamparth I, Herzog A, Hirsch A (1996)

Publication Type: Journal article, Original article

Publication year: 1996


Original Authors: Lamparth I., Herzog A., Hirsch A.

Publisher: Elsevier

Book Volume: 52

Pages Range: 5065-5075

Journal Issue: 14

DOI: 10.1016/0040-4020(96)00114-7


Regioselective formations of [60]fullerene derivatives with octohedral addition patterns are described. Via template activation with 9,10-dimethylanthracene T(h)-symmetric as well as mixed C(2v)-symmetric hexaadducts are obtained in one step starting from C or C(2v)-symmetric monoadducts in comparatively high yields. The thermally induced cycloreversion of azide from fullerotriazolines with five methano bridges in octahedral positions allows also the synthesis of the C(2v)-symmetric pentaadduct C(COOEt) in large quantities, which shows that azides can be used as protecting groups for 6-6 double bonds. The remaining octahedral double bonds in C(COOEt) is by far the most reactive in the molecule, which also allows an extremely regioselective synthesis of hexaadducts with an octahedral addition pattern. The specific oxidation of the reactive octahedral double bond of C(COOEt) leads to an unusual dioxetane formation.

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Lamparth, I., Herzog, A., & Hirsch, A. (1996). Synthesis of [60]fullerene derivatives with an octahedral addition pattern. Tetrahedron, 52(14), 5065-5075.


Lamparth, Iris, Andrea Herzog, and Andreas Hirsch. "Synthesis of [60]fullerene derivatives with an octahedral addition pattern." Tetrahedron 52.14 (1996): 5065-5075.

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