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- Title
Fullerene-Acetylene Molecular Scaffolding: Chemistry of 2-functionalized 1-ethynylated C<sub>60</sub>, oxidative homocoupling, hexakis-adduct formation, and attempted synthesis of C.
- Authors
Timmerman, Peter; Witschel, Lars E.; Diederich, François; Boudon, Corinne; Gisselbrecht, Jean-Paul; Gross, Maurice
- Abstract
On the way to the fullerene-acetylene hybrid carbon allotropes 2 and 6, the oxidative homocoupling of the 2-functionalized 1-ethynylated C60 derivatives 11, 12, 14, and 15 was investigated. Under Glaser-Hay conditions, the two soluble dumbbell-shaped bisfullerenes 17 and 18, with two C60 moieties linked by a buta-1,3-diynediyl bridge, were formed in 52 and 82% yield, respectively ( Scheme 2). Cyclic-voltammetric measurements revealed that there is no significant electronic communication between the two fullerene spheres via the buta-1,3-diynediyl linker. Removal of the 3,4,5,6-tetrahydro-2 H-pyran-2-yl (Thp) protecting groups in 18 gave in 80% yield the highly insoluble dumbbell 19 with methanol groups in the 2,2′-positions of the buta-1,3-diynediyl-bridged carbon spheres. Attempted conversion of 19 to the all-carbon dianion 6 (C
- Publication
Helvetica Chimica Acta, 1996, Vol 79, Issue 1, p6
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19960790103