Formation of new organoselenium heterocycles and ring reduction of 10-membered heterocycles into seven-membered heterocycles

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

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)

Abstract

Reacting 2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide [{PhP(Se)(mu-Se)}(2)], Woollins' reagent, with an equivalent of aromatic diol in refluxing toluene afforded 10-membered phosphorus-selenium heterocycles 1 and 2 with an O-P(Se)-Se-Se-P(Se)-O linkage. Two equivalents of aromatic diol and Woollins' reagent in refluxing toluene gave seven-membered phosphorus-selenium heterocycles 3 and 4 with an O-P(Se)-O linkage together with 10-membered phosphorus-selenium heterocycles 1 and 2. It was also found that the diphosphorus species O-P(Se)-Se-Se-P(Se)-O rings 1 and 2 could be readily ring contracted into the monophosphorus rings 3 and 4 in almost quantitative yields via further reaction with another equivalent of corresponding aromatic diol. One representative X-ray structure is reported. (C) 2011 Published by Elsevier Ltd.

Original languageEnglish
Pages (from-to)805-808
Number of pages4
JournalPolyhedron
Volume30
Issue number5
DOIs
Publication statusPublished - 24 Mar 2011

Keywords

  • Woollins reagent
  • Aromatic diol
  • Phosphorus-selenium heterocycle
  • Ring reduction
  • P-SE HETEROCYCLES
  • RAY CRYSTAL-STRUCTURES
  • ELECTROPHILIC SELENIUM
  • WOOLLINS REAGENT
  • METAL-COMPLEXES
  • REACTIVITY
  • CHEMISTRY
  • (PHP(SE)(MU-SE))(2)
  • CYANAMIDES
  • ANHYDRIDE

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