標題: [3+2] Cycloaddition of Dialkyl (E)-Hex-2-en-4-ynedioates to [60]Fullerene by Phosphane-Promoted Tandem alpha(delta ')-Michael Additions
作者: Chuang, Shih-Ching
Deng, Jie-Cheng
Chan, Fu-Wei
Chen, Sheng-Yuan
Huang, Wei-Je
Lai, Li-Hsiang
Rajeshkumar, Venkatachalam
應用化學系
Department of Applied Chemistry
關鍵字: Fused-ring systems;Cycloaddition;Fullerenes;Phosphanes;Ylides;Michael addition
公開日期: 1-五月-2012
摘要: Organophosphanes promote the [3+2] cycloaddition reactions of dialkyl (E)-hex-2-en-4-ynedioates and [60]fullerene, giving a series of cyclopenteno-fullerenes 3ak bearing phosphorus ylides. This cycloaddition reaction is initiated by the attack of nucleophilic phosphanes at the a(d')-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 C60 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-C61 methyl butyrate, which indicates that these new derivatives possess higher LUMO energy levels.
URI: http://hdl.handle.net/11536/15996
ISSN: 1434-193X
期刊: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume: 
Issue: 13
結束頁: 2606
顯示於類別:期刊論文


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