4.8 Article

Hydroxide-Initiated Conversion of Aromatic Nitriles to Imidazolines: Fullerenes vs TCNE

Journal

ORGANIC LETTERS
Volume 15, Issue 18, Pages 4646-4649

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol401834j

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Funding

  1. NSFC [21172212, 20972150, 21202157]
  2. Solar Energy Initiative of the Chinese Academy of Sciences [KGCX2-YW-399+9]

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Transformation of aromatic nitriles to imidazolines has been achieved under basic conditions with the electron-deficient C-60 and C-70 fullerenes, but not with the electron-deficient olefin of tetracyanoethylene (TCNE). In situ UV-vis-NIR indicates that the ability of RC60- to undergo single-electron transfer (SET) to C-60 is crucial for the reaction.

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