Acetylene-substituted phosphane oxides: Building blocks for macrocycles

Sander G.A. Van Assema, G. Bas De Jong, Andreas W. Ehlers, Frans J.J. De Kanter, Marius Schakel, Anthony L. Spek, Martin Lutz, Koop Lammertsma

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)


Phosphorus-based macrocycles with acetylenic scaffolds have been built from acetylene-substituted phosphane oxides that were formed from diisopropylphosphoramidic dibromide (3) and an acetylenic Grignard reagent. The four-and six-edged macrocycles 15 and 16, in which the iPr2NP(O) units are connected through 1,3-butadiyne rods, were obtained from the monosilylated derivative of iPr2NP(O)(C2H)2 (7) by multiple acetylene coupling reactions under oxidative Hay conditions. Reaction of iPr2NP(O)(Br)2 (3) with lithiated 1,2-diethynylbenzene gave a mixture of cis and trans monocyclic bis(phosphane oxide) 18. An X-ray crystal structure determination of the trans isomer shows the ring structure to adopt a puckered form.

Original languageEnglish
Pages (from-to)2405-2412
Number of pages8
JournalEuropean Journal of Organic Chemistry
Issue number15
Publication statusPublished - 2007
Externally publishedYes


  • Alkynes
  • Cross-coupling
  • Macrocycles
  • Phosphanes
  • Phosphorus heterocycles

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry


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