Efficient synthesis of cyclic β-oxophosphoranes by microwave-assisted reaction of cyclic phosphine oxides and dialkyl acetylenedicarboxylates

György Keglevich, Eszter Dudás, Melinda Sipos, Dóra Lengyel, Krisztina Ludányi

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28 Citations (Scopus)

Abstract

The inverse Wittig-type reaction of a series of 2,4,6-trialkylphenyl cyclic phosphine oxides 3, 5, 7, 9, 11, 13, 15, 18 and 20 and dialkyl acetylenedicarboxylate giving β-oxophosphoranes 4, 6, 8, 10, 12, 14, 16, 19 and 21, respectively, can be accomplished in a convenient way under microwave conditions. At 150 °C, the MW-assisted reaction is more efficient and becomes 50-fold faster as compared to the thermal transformation. A further advantage is that the 2,5-dihydrophosphole moiety of the 2,4,6- triisopropylphenyl derivative 3 does not undergo double-bond rearrangement and that the 2,4,6-trimethylphenyl substrates 11 and 13, otherwise inactive in the reaction under discussion, could also be converted to β-oxophosphoranes 12 and 14. A series of new products 4Bb, 12, 14, 16b, 19 and 21 have been made available.

Original languageEnglish
Pages (from-to)1365-1369
Number of pages5
JournalSynthesis
Issue number8
DOIs
Publication statusPublished - Apr 19 2006

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Keywords

  • Alkyne derivatives
  • Cyclic phosphine oxides
  • Inverse-Wittig reactions
  • Microwave synthesis
  • Phosphoranes
  • Ylides

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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