Synthesis of 2,5-bis(phosphinoylmethyl)- and 2,5-bis(thiophosphinoylmethyl) -thiophenes

Jean Michel Camus, Sylvie Pailloux, Cornel Edicome Shirima, Robert T. Paine

Research output: Contribution to journalArticlepeer-review

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Abstract

The 2,5-bis(phosphinoylmethyl)-thiophenes [(Oct)(EtO)P(O)CH 2]2C4H2S and [(Ph)(EtO)P(O)CH 2]2C4H2S are obtained from the appropriate phosphites, RP(OEt)2 (R=Oct, Ph) and (BrCH 2)2C4H2S by using Arbusov reaction conditions. The analog [(Oct)2P(O)CH2]2C 4H2S is more conveniently obtained via the reaction of the phosphono-Grignard reagent (Oct)2P(O)MgBr and (BrCH 2)2C4H2S. An improved alternate Arbusov synthesis of the known [Ph2P(O)CH2] 2C4H2S is described along with its conversion to [Ph2P(S)CH2]2C4H2S via Lawesson chemistry. The new compounds are characterized by MS, IR and NMR methods, and the molecular structures of [Ph2P(O)CH2] 2C4H2S and [Ph2P(S)CH 2]2C4H2S have been confirmed by single crystal X-ray diffraction methods.

Original languageEnglish (US)
Pages (from-to)25-36
Number of pages12
JournalMain Group Chemistry
Volume10
Issue number1
DOIs
StatePublished - 2011

Keywords

  • Synthesis
  • X-ray crystal sstructure
  • phosphine oxide
  • phosphine sulfide
  • phosphite
  • thiophene

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