Effect of the CO2H groups of carboxylated triarylphosphines on (COD) RhCl(PAr3) -catalyzed isomerization of 1-octen-3-ol under phase transfer conditions

Herbert Schumann, Vadde Ravindar, Larisa Meltser, Waël Baidossi, Yoel Sasson, Jochanan Blum*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

41 Scopus citations

Abstract

Water soluble sodium salts of (COD)RhCl(PAr3), where PAr3 is Ph2P(C6H4-2-COOH), Ph2P(C6H4-3-COOH), Ph2P(C6H4-4-COOH), PhP(C6H4-3-COOH)2, or P(C6H4-3-COOH)3, catalyze under phase transfer conditions the isomerization of 1-octen-3-ol to 3-octanone. The reaction rate depends on the position and number of the carboxyl groups in the phosphine ligand. (COD)RhCl[Ph2P(C6H4-2-C6H4-COOH], which exists as an equilibrium mixture with (COD)(H)RhCl(-OCOC6H4-2-PPh2) more reactive than the hydride-free catalysts. A hydride addition-elimination mechanism is suggested as the major pathway for the catalytic process.

Original languageEnglish
Pages (from-to)55-61
Number of pages7
JournalJournal of Molecular Catalysis A: Chemical
Volume118
Issue number1
DOIs
StatePublished - 11 Apr 1997

Keywords

  • 1-Octen-3-ol
  • Double bond migration
  • Phase transfer catalysis
  • Rhodium

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