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

doi:10.1016/S1381-1169(96)00374-3

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

Institute of Chemistry

Research output: Contribution to journal › Article › peer-review

42 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 language	English
Pages (from-to)	55-61
Number of pages	7
Journal	Journal of Molecular Catalysis A: Chemical
Volume	118
Issue number	1
DOIs	https://doi.org/10.1016/S1381-1169(96)00374-3
State	Published - 11 Apr 1997

Keywords

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

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10.1016/S1381-1169(96)00374-3

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

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.",

keywords = "1-Octen-3-ol, Double bond migration, Phase transfer catalysis, Rhodium",

author = "Herbert Schumann and Vadde Ravindar and Larisa Meltser and Wa{\"e}l Baidossi and Yoel Sasson and Jochanan Blum",

year = "1997",

month = apr,

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doi = "10.1016/S1381-1169(96)00374-3",

language = "אנגלית",

volume = "118",

pages = "55--61",

journal = "Journal of Molecular Catalysis A: Chemical",

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T1 - Effect of the CO2H groups of carboxylated triarylphosphines on (COD) RhCl(PAr3) -catalyzed isomerization of 1-octen-3-ol under phase transfer conditions

AU - Schumann, Herbert

AU - Ravindar, Vadde

AU - Meltser, Larisa

AU - Baidossi, Waël

AU - Sasson, Yoel

AU - Blum, Jochanan

PY - 1997/4/11

Y1 - 1997/4/11

N2 - 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.

AB - 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.

KW - 1-Octen-3-ol

KW - Double bond migration

KW - Phase transfer catalysis

KW - Rhodium

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AN - SCOPUS:0030974036

SN - 1381-1169

VL - 118

SP - 55

EP - 61

JO - Journal of Molecular Catalysis A: Chemical

JF - Journal of Molecular Catalysis A: Chemical

IS - 1

ER -

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

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