Novel five- to ten-membered organoselenium heterocycles from the selenation of aromatic diols

Guoxiong Hua, Amy Fuller, Alexandra M. Z. Slawin, J Derek Woollins

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24 Citations (Scopus)

Abstract

Reaction of Woollins' reagent ― WR, 2,4-bis(phenyl)-1,3-diselenadiphosphetane 2,4-diselenide [{PhP(Se)(μ-Se)}2] ― with aromatic diols in refluxing toluene afforded a series of novel five- to ten-membered phosphorus-selenium heterocycles 110 with an O–P(Se)–O or O–P(Se)–Se–P(Se)–O or O–P(Se)–O–P(Se)–O linkage in 12–74 % isolated yields. It was found that the diphosphorus species O–P(Se)–Se–P(Se)–O rings could be readily reduced into the monophosphorus species O–P(Se)–O rings in almost quantitative yields via further reaction with another equivalent of corresponding aromatic diol. All new compounds have been characterized by IR, 1H NMR, 13C NMR, 31P NMR, 77Se NMR, mass spectrometry and elemental analysis or accurate mass measurement. Seven representative X-ray structures are reported.
Original languageEnglish
Pages (from-to)2607-2615
Number of pages9
JournalEuropean Journal of Organic Chemistry
Volume2010
Issue number13
DOIs
Publication statusPublished - May 2010

Keywords

  • Main group elements
  • Heterocycles
  • Phosphorus
  • Selenium
  • Organoselenium compounds
  • P-SE heterocycles
  • Ray crystal-structures
  • Woollins reagent
  • Reactivity
  • (PHP(SE)(MU-SE))(2)
  • Cyanamides
  • Anhydride
  • Compplexes

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