Abstract
Organophosphanes promote the [3+2] cycloaddition reactions of dialkyl (E)-hex-2-en-4-ynedioates and [60]fullerene, giving a series of cyclopenteno-fullerenes 3a-k bearing phosphorus ylides. This cycloaddition reaction is initiated by the attack of nucleophilic phosphanes at the α(δ')-C atom of the dialkyl (E)-hex-2-en-4-ynedioate, which generates a 1,3-dipolar species. These 1,3-dipoles then react with C 60 followed by intramolecular cyclization to give cyclopenteno-fullerenes in moderate-to-good yields. In a cyclic voltmmetry study, these novel fullerenes show a larger cathodic shift in their first reduction potential relative to [6,6]phenyl-C 61 methyl butyrate, which indicates that these new derivatives possess higher LUMO energy levels.
Original language | English |
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Pages (from-to) | 2606-2613 |
Number of pages | 8 |
Journal | European Journal of Organic Chemistry |
Issue number | 13 |
DOIs | |
State | Published - 1 May 2012 |
Keywords
- Cycloaddition
- Fullerenes
- Fused-ring systems
- Michael addition
- Phosphanes
- Ylides