Redox Reactions of a Stable Dialkylphosphinyl Radical

Fumiya Hirakawa, Hitomi Ichikawa, Shintaro Ishida, Takeaki Iwamoto

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)


A stable dialkylphosphinyl radical, 2,2,5,5-tatrakis(trimethylsilyl)-1-phosphacyclopentan-1-yl (RH2P), showed both irreversible one-electron oxidation and reduction peaks at -0.24 and -2.29 V vs ferrocene/ferrocenium couple. One-electron reduction of RH2P with KC8 in the presence of 18-crown-6 (18-c-6) or [2.2.2]cryptand (crypt-222) gave the corresponding phosphides [K(18-c-6)]+[RH2P]- and [K(crypt-222)]+[RH2P]-. Whereas [K(18-c-6)]+[RH2P]- exists as a contact ion pair, [K(crypt-222)]+[RH2P]- exists as a solvent-separated ion pair in the solid state. Reaction of RH2P with AgOTf afforded an unexpected product, a silver(I) phosphaalkene complex. (Chemical Equation Presented).

Original languageEnglish
Pages (from-to)2714-2716
Number of pages3
Issue number12
Publication statusPublished - 2015 Jun 22

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry


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