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Title: Preparation and identification of bis(formylmethano)[60]fullerene isomers: the first systematic study on bifunctionalized [60]fullerenes with dissymmetric addends
Authors: Ito, Hiroshi
Ishida, Yasuhiro
Saigo, Kazuhiko
Issue Date: 12-Dec-2005
Publisher: Elsevier
Journal Title: Tetrahedron Letters
Volume: 46
Issue: 50
Start Page: 8757
End Page: 8760
Abstract: Fourteen isomers of bis(formylmethano)C60 were isolated and characterized. A mixture of the bisadducts was obtained by the reaction of C60 with an α-formylsulfonium ylide, and then separated into fifteen fractions by preparative HPLC, preparative TLC, and recycling preparative HPLC. Fourteen of fifteen fractions were found to consist of a single isomer, respectively, which were assigned to the trans-2 (3 diastereo-isomers), trans-3 (3 diastereo-isomers), trans-4 (3 diastereo-isomers), equarorial (2 diastereo-isomers), and cis-2 (3 diastereo-isomers) bisadducts by the comparison of their UV/vis spectra with those of the bisadducts obtained by the Bingel-Hirsch reaction. The 1H- and 13C-NMR analysis, the transformation of the formyl groups, and the dipole moment calculation clarified the stereochemistry of the subsitutents on the two cyclopropane bridge-head carbons (in/in, in/out, and out/out)
Rights: © 2005 Elsevier Ltd. All rights reserved.
DOI: http://dx.doi.org/10.1016/j.tetlet.2005.10.027
Type: Journal Article
URI: http://hdl.handle.net/10173/784
Appears in Collections:西郷, 和彦 (SAIGO, Kazuhiko)

Please use this identifier to cite or link to this item: http://hdl.handle.net/10173/784

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