An extremely long-lived singlet 4,4-dimethoxy-3,5-diphenylpyrazolidine-3,5- diyl derivative: A notable nitrogen-atom effect on intra- and intermolecular reactivity

Manabu Abe*, Emi Kubo, Koichi Nozaki, Takashi Matsuo, Takashi Hayashi

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

36 Scopus citations

Abstract

Life in the fast lane: An extremely long-lived singlet state of 4,4-dimethoxy-3,5-diphenylpyrazoline-3,5-diyl (1; τ = 9.67 ms at room temperature) is reported, which affords intramolecularly the oxygen-migration product and reacts intermolecularly with 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) to give the cycloaddition product. The diradical intermediate was characterized by its absorption band at 645 nm. (Chemical Equation Presented).

Original languageEnglish
Pages (from-to)7828-7831
Number of pages4
JournalAngewandte Chemie - International Edition
Volume45
Issue number46
DOIs
StatePublished - 2006/11/27

Keywords

  • Photolysis
  • Quantum chemical calculations
  • Reactive intermediates
  • Singlet diradicals

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry

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