Isomerization of olefin carboxylic esters catalyzed by nickel and palladium compounds

Xiaotai Wang; L. Keith Woo

doi:10.1016/S1381-1169(97)00213-6

Isomerization of olefin carboxylic esters catalyzed by nickel and palladium compounds

Xiaotai Wang, L. Keith Woo^*

^*Corresponding author for this work

Iowa State University

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

15 Citations (Scopus)

Abstract

The Group 10 complex trans-Pd(C₆H₅CN)₂Cl₂Cl₂ and acidic solutions of Ni[P(OEt)₃]₄ effectively catalyze the stereoselective isomerization of C=C double bonds in olefinic esters. With acidic solutions of Ni[P(OEt)₃]₄, only 4-pentenoate is produced from 3-pentenoate at early times. However, in the presence of excess phosphite, 2-pentenoate is the only positional isomer produced (61% yield). In the absence of excess phosphite, a kinetically controlled process is proposed to explain the initial formation of 4-pentenoate. With the Pd catalyst, no 4-pentenoate is observed. For example, trans-Pd(C₆H₅CN)₂Cl₂ selectively produces 2-pentenoate from 3-pentenoate (58%).

Original language	English
Pages (from-to)	171-176
Number of pages	6
Journal	Journal of Molecular Catalysis A: Chemical
Volume	130
Issue number	1-2
DOIs	https://doi.org/10.1016/S1381-1169(97)00213-6
Publication status	Published - 12 Mar 1998
Externally published	Yes

Keywords

Catalysis
Isomerization
Nickel
Olefin
Palladium

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10.1016/S1381-1169(97)00213-6

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@article{e37cbf70464f48e1a36b3991873e1c3a,

title = "Isomerization of olefin carboxylic esters catalyzed by nickel and palladium compounds",

abstract = "The Group 10 complex trans-Pd(C6H5CN)2Cl2Cl2 and acidic solutions of Ni[P(OEt)3]4 effectively catalyze the stereoselective isomerization of C=C double bonds in olefinic esters. With acidic solutions of Ni[P(OEt)3]4, only 4-pentenoate is produced from 3-pentenoate at early times. However, in the presence of excess phosphite, 2-pentenoate is the only positional isomer produced (61% yield). In the absence of excess phosphite, a kinetically controlled process is proposed to explain the initial formation of 4-pentenoate. With the Pd catalyst, no 4-pentenoate is observed. For example, trans-Pd(C6H5CN)2Cl2 selectively produces 2-pentenoate from 3-pentenoate (58%).",

keywords = "Catalysis, Isomerization, Nickel, Olefin, Palladium",

author = "Xiaotai Wang and Woo, {L. Keith}",

note = "Funding Information: Financial support of this work was provided by the Iowa Soybean Promotion Board.",

year = "1998",

month = mar,

day = "12",

doi = "10.1016/S1381-1169(97)00213-6",

language = "English",

volume = "130",

pages = "171--176",

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

issn = "1381-1169",

number = "1-2",

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TY - JOUR

T1 - Isomerization of olefin carboxylic esters catalyzed by nickel and palladium compounds

AU - Wang, Xiaotai

AU - Woo, L. Keith

N1 - Funding Information: Financial support of this work was provided by the Iowa Soybean Promotion Board.

PY - 1998/3/12

Y1 - 1998/3/12

N2 - The Group 10 complex trans-Pd(C6H5CN)2Cl2Cl2 and acidic solutions of Ni[P(OEt)3]4 effectively catalyze the stereoselective isomerization of C=C double bonds in olefinic esters. With acidic solutions of Ni[P(OEt)3]4, only 4-pentenoate is produced from 3-pentenoate at early times. However, in the presence of excess phosphite, 2-pentenoate is the only positional isomer produced (61% yield). In the absence of excess phosphite, a kinetically controlled process is proposed to explain the initial formation of 4-pentenoate. With the Pd catalyst, no 4-pentenoate is observed. For example, trans-Pd(C6H5CN)2Cl2 selectively produces 2-pentenoate from 3-pentenoate (58%).

AB - The Group 10 complex trans-Pd(C6H5CN)2Cl2Cl2 and acidic solutions of Ni[P(OEt)3]4 effectively catalyze the stereoselective isomerization of C=C double bonds in olefinic esters. With acidic solutions of Ni[P(OEt)3]4, only 4-pentenoate is produced from 3-pentenoate at early times. However, in the presence of excess phosphite, 2-pentenoate is the only positional isomer produced (61% yield). In the absence of excess phosphite, a kinetically controlled process is proposed to explain the initial formation of 4-pentenoate. With the Pd catalyst, no 4-pentenoate is observed. For example, trans-Pd(C6H5CN)2Cl2 selectively produces 2-pentenoate from 3-pentenoate (58%).

KW - Catalysis

KW - Isomerization

KW - Nickel

KW - Olefin

KW - Palladium

UR - http://www.scopus.com/inward/record.url?scp=0032510570&partnerID=8YFLogxK

U2 - 10.1016/S1381-1169(97)00213-6

DO - 10.1016/S1381-1169(97)00213-6

M3 - Article

AN - SCOPUS:0032510570

SN - 1381-1169

VL - 130

SP - 171

EP - 176

JO - Journal of Molecular Catalysis A: Chemical

JF - Journal of Molecular Catalysis A: Chemical

IS - 1-2

ER -

Isomerization of olefin carboxylic esters catalyzed by nickel and palladium compounds

Abstract

Keywords

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