Synthesis of 1-aryl-1,2,3,4,5,6-hexahydrophosphinine 1-oxides

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Abstract

Possibilities for the synthesis of 1-(2,4,6-triisopropylphenyl-) 1,2,3,4,5,6-hexahydrophosphinine oxide (2) have been explored. The trivial method based on the hydrogenation of the corresponding dihydrophosphinine oxides (8a-e) was suitable only for the preparation of hexahydrophosphinine oxides containing a trimethylphenyl or methylphenyl group on the phosphorus atom (9a-c). The triisopropylphenyl product (2) was synthesized by the stepwise reduction of the double bonds of starting material 1. Hence, the ring contraction side reaction, observed during the catalytic hydrogenation, could be eliminated. The unusual reactivity was studied by quantum chemical calculations.

Original languageEnglish
Pages (from-to)4159-4169
Number of pages11
JournalSynthetic Communications
Volume34
Issue number22
DOIs
Publication statusPublished - Nov 29 2004

Keywords

  • Dihydrophosphinine oxides
  • Reduction
  • Ring contraction hexahydrophosphinine oxides
  • Theoretical calculations

ASJC Scopus subject areas

  • Organic Chemistry

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