Studies on Phosphorus-Chalcogen Bond Systems Stabilized by Bulky Substituents.

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  • Toyota Kozo
    Department of Chemistry, Graduate School of Science, Tohoku University
  • Yoshifuji Masaaki
    Department of Chemistry, Graduate School of Science, Tohoku University

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  • かさ高い置換基の安定化効果を利用した，リン‐カルコゲン結合系の研究
  • カサダカイ チカンキ ノ アンテイカ コウカ オ リヨウ シタ リン カルコゲン ケツゴウケイ ノ ケンキュウ

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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. Deselenation 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.

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