[3+2] Cycloaddition of dialkyl (E)-hex-2-en-4-ynedioates to [60]fullerene by phosphane-promoted tandem α(δ')-Michael additions

Shih-Ching Chuang*, Jie Cheng Deng, Fu Wei Chan, Sheng Yuan Chen, Wei Je Huang, Li Hsiang Lai, Venkatachalam Rajeshkumar

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

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 languageEnglish
Pages (from-to)2606-2613
Number of pages8
JournalEuropean Journal of Organic Chemistry
Issue number13
DOIs
StatePublished - 1 May 2012

Keywords

  • Cycloaddition
  • Fullerenes
  • Fused-ring systems
  • Michael addition
  • Phosphanes
  • Ylides

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