Hydrogenolysis and Homologation of Linear and Branched Pentenes on Ru/SiO2 Catalysts: Implication in the Mechanism of C-C Bond Formation and Cleavage on Metal Surfaces

Eloy Rodriguez; Michel Leconte; Jean Marie Basset; Katsumi Tanaka; Ken Ichi Tanaka

doi:10.1021/ja00209a043

Hydrogenolysis and Homologation of Linear and Branched Pentenes on Ru/SiO₂ Catalysts: Implication in the Mechanism of C-C Bond Formation and Cleavage on Metal Surfaces

Eloy Rodriguez, Michel Leconte, Jean Marie Basset^*, Katsumi Tanaka, Ken Ichi Tanaka

^*Corresponding author for this work

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

25 Scopus citations

Abstract

Hydrogenolysis and homologation of 1-pentene to butenes and hexenes take place simultaneously and at the same rate over a Ru/SiO₂ catalyst at 110 °C, suggesting that these two reactions are mechanistically related. ¹³C labeling experiments indicate that C-C cleavage occurs at the double bond of l-pentene-1-¹³C leading to unlabeled 1-butene and labeled hexenes. The product distribution in the hydrogenolysis of 1-pentene, 2-pentenes, 3-methyl-1-butene, 2-methyl-2-butene, and 2-methyl-1-butene is accounted for by a carbene-olefin mechanism, which can therefore be considered as a reasonable common path for the formation and cleavage of carbon-carbon bonds on metal surfaces.

Original language	English (US)
Pages (from-to)	275-278
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	110
Issue number	1
DOIs	https://doi.org/10.1021/ja00209a043
State	Published - Jan 1988
Externally published	Yes

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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title = "Hydrogenolysis and Homologation of Linear and Branched Pentenes on Ru/SiO2 Catalysts: Implication in the Mechanism of C-C Bond Formation and Cleavage on Metal Surfaces",

abstract = "Hydrogenolysis and homologation of 1-pentene to butenes and hexenes take place simultaneously and at the same rate over a Ru/SiO2 catalyst at 110 °C, suggesting that these two reactions are mechanistically related. 13C labeling experiments indicate that C-C cleavage occurs at the double bond of l-pentene-1-13C leading to unlabeled 1-butene and labeled hexenes. The product distribution in the hydrogenolysis of 1-pentene, 2-pentenes, 3-methyl-1-butene, 2-methyl-2-butene, and 2-methyl-1-butene is accounted for by a carbene-olefin mechanism, which can therefore be considered as a reasonable common path for the formation and cleavage of carbon-carbon bonds on metal surfaces.",

author = "Eloy Rodriguez and Michel Leconte and Basset, {Jean Marie} and Katsumi Tanaka and Tanaka, {Ken Ichi}",

year = "1988",

month = jan,

doi = "10.1021/ja00209a043",

language = "English (US)",

volume = "110",

pages = "275--278",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "1",

}

Hydrogenolysis and Homologation of Linear and Branched Pentenes on Ru/SiO₂ Catalysts: Implication in the Mechanism of C-C Bond Formation and Cleavage on Metal Surfaces. / Rodriguez, Eloy; Leconte, Michel; Basset, Jean Marie et al.
In: Journal of the American Chemical Society, Vol. 110, No. 1, 01.1988, p. 275-278.

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

TY - JOUR

T1 - Hydrogenolysis and Homologation of Linear and Branched Pentenes on Ru/SiO2 Catalysts

T2 - Implication in the Mechanism of C-C Bond Formation and Cleavage on Metal Surfaces

AU - Rodriguez, Eloy

AU - Leconte, Michel

AU - Basset, Jean Marie

AU - Tanaka, Katsumi

AU - Tanaka, Ken Ichi

PY - 1988/1

Y1 - 1988/1

N2 - Hydrogenolysis and homologation of 1-pentene to butenes and hexenes take place simultaneously and at the same rate over a Ru/SiO2 catalyst at 110 °C, suggesting that these two reactions are mechanistically related. 13C labeling experiments indicate that C-C cleavage occurs at the double bond of l-pentene-1-13C leading to unlabeled 1-butene and labeled hexenes. The product distribution in the hydrogenolysis of 1-pentene, 2-pentenes, 3-methyl-1-butene, 2-methyl-2-butene, and 2-methyl-1-butene is accounted for by a carbene-olefin mechanism, which can therefore be considered as a reasonable common path for the formation and cleavage of carbon-carbon bonds on metal surfaces.

AB - Hydrogenolysis and homologation of 1-pentene to butenes and hexenes take place simultaneously and at the same rate over a Ru/SiO2 catalyst at 110 °C, suggesting that these two reactions are mechanistically related. 13C labeling experiments indicate that C-C cleavage occurs at the double bond of l-pentene-1-13C leading to unlabeled 1-butene and labeled hexenes. The product distribution in the hydrogenolysis of 1-pentene, 2-pentenes, 3-methyl-1-butene, 2-methyl-2-butene, and 2-methyl-1-butene is accounted for by a carbene-olefin mechanism, which can therefore be considered as a reasonable common path for the formation and cleavage of carbon-carbon bonds on metal surfaces.

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U2 - 10.1021/ja00209a043

DO - 10.1021/ja00209a043

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AN - SCOPUS:0024279681

SN - 0002-7863

VL - 110

SP - 275

EP - 278

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 1

ER -

Hydrogenolysis and Homologation of Linear and Branched Pentenes on Ru/SiO₂ Catalysts: Implication in the Mechanism of C-C Bond Formation and Cleavage on Metal Surfaces

Abstract

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