A New Synthesis of (PhPSe2)2 (Woollins Reagent), and Its Use in the Synthesis of Novel P-Se Heterocycles

IP Gray, P Bhattacharyya, Alexandra Martha Zoya Slawin, John Derek Woollins

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114 Citations (Scopus)

Abstract

A new and improved method for the preparation of (PhPSe2)(2) (Woollins reagent (WR), 1) is reported. Reaction of dichlorophenylphosphine with Na2Se, (prepared from the reaction of elemental selenium and sodium in liquid ammonia) gives WR with excellent purity, high yield and on a larger scale than was previously possible. Four novel phosphorus-selenium heterocycles, including a spirocyclic heterocycle exhibiting a four-membered P2SeC ring, were obtained from the reaction of WR with two reactive substrates (diphenylcyclopropenone and methyl phenylpropiolate). Useful selenocarbonyl and thiocarbonyl compounds were obtained from the reaction of both WR and Lawesson's reagent with diphenylcyclopropenone. All new compounds were characterised spectroscopically and three demonstrative X-ray structures are reported.

Original languageEnglish
Pages (from-to)6221-6227
Number of pages7
JournalChemistry - A European Journal
Volume11
Issue number21
DOIs
Publication statusPublished - 21 Oct 2005

Keywords

  • heterocycles
  • phosphorus
  • selenium
  • Woollins reagent
  • X-ray structure
  • PHOSPHORUS-SELENIUM HETEROCYCLES
  • RAY CRYSTAL-STRUCTURES
  • LAWESSONS REAGENT
  • THIONATION REACTIONS
  • (PHP(SE)(MU-SE))(2)
  • CYANAMIDES

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