Studies on phosphorus-chalcogen bond systems stabilized by bulky substituents

Kozo Toyota, Masaaki Yoshifuji

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1 Citation (Scopus)


Reactions of sterically hindered primary phosphines with elemental sulfur or selenium are reviewed. (2,4,6-Tri-t-butylphenyl) phosphine reacted with an excess amount of elemental sulfur in the presence of a catalytic amount of base to give the corresponding dithioxophosphorane via the phosphine sulfide. Dithioxophosphoranes and diselenoxophosphoranes bearing the 2,4-di-t-butyl-6-(dialkylamino)phenyl group were prepared by a similar method. These compounds are more stable than the corresponding 2,4,6-tri-t-butylphenyl derivatives. Deselection reaction of stabilized (selenoxo)(thioxo)phosphoranes and diselenoxophosphoranes afforded thioxophosphines and selenoxophosphines, respectively. On the other hand, reaction of (2,4-di-t-butyl-6-methoxyphenyl) phosphine with sulfur gave trans- and cis-1,3,2,4-dithiadiphosphetane-2,4-disulfides via dithioxophosphorane. The monomeric form of dithioxophosphorane, which can be generated from dithiadiphosphetane disulfides by heating, reacted with benzophenone to give thiobenzophenone. (2,4-Di-t-butyl-6-methoxyphenyl) phosphine reacted with selenium to give 1,2,3,5,7-pentaselena-4,6,8-triphosphocane, which was used to convert amides into thioamides.

Original languageEnglish
Pages (from-to)208-217
Number of pages10
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Issue number3
Publication statusPublished - 2000 Mar
Externally publishedYes


  • Diselenoxophosphorane
  • Dithioxophosphorane
  • Kinetic stabilization
  • Main group element
  • Multiple bond
  • Selenoxophosphine
  • Steric protection
  • Thermodynamic stabilization
  • Thioxophosphine

ASJC Scopus subject areas

  • Organic Chemistry


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