Phosphorus-centered radical stabilized by bulky alkyl group and related compounds

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Dicoordinate phosphorus-centered radical (phosphinyl radical) is a fascinating reactive intermediate in phosphorus chemistry because it has a bifunctional phosphorus center owing to an unpaired electron and a lone pair. I report herein synthesis, structure, properties, and various reactions of the first stable dialkylphosphinyl radical, 2,2,5,5-tetrakis (trimethylsilyl)-1-phosphacyclopentane-1-yl (8), which is monomeric both in solution and in the solid state. Palladium complex bearing two phosphinyl radicals as ligands (24) is also synthesized by the ligand exchange reaction of tetrakis (trimethylphosphine) palladium with two equivalents of radical 8. Complex 24 shows unique phosphorus-palladium double bond character. Antimony and bismuth analogues of phosphinyl radicals are elusive species but are thought to be important intermediates. We have succeeded in the observation of antimony- and bismuth-centered radicals (30 and 31) as persistent species in solution by the dissociation of the corresponding dimer.

Original languageEnglish
Pages (from-to)885-894
Number of pages10
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Issue number9
Publication statusPublished - 2015


  • Antimony
  • Bismuth
  • Epr
  • Kinetic stabilization
  • Phosphorus
  • Radical
  • Redox
  • Transition metal complex
  • X-ray structural analysis


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