Low- and high-temperature hydrogenative ring-opening of alkyl-substituted cyclopropanes and methyloxirane over Pd/SiO2 catalyst: detection of β-hydride by a chemical method

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Abstract

The hydrogenative ring-opening of five alkyl-substituted cyclopropanes and of methyl-oxirane on Pd/SiO2 was studied at different temperatures in a closed circulation reactor. For cyclopropanes, the ring opens through simple hydrogenation, giving exclusively saturated hydrocarbons, whereas alcohols (hydrogenation), oxo compounds (isomerization) and also cracking products are produced from methyloxirane. The substituents exert significant effects on the regioselectivity of the reactions for both type of molecules. For the cyclic hydrocarbons, mechanistic pathways are discussed on the basis of the stereochemistry of the compounds and the characteristic features of the ring-opening rate vs. H2-pressure functions. Finally, a chemical method is proposed for the detection of β-hydride.

Original languageEnglish
Pages (from-to)43-54
Number of pages12
JournalJournal of Molecular Catalysis
Volume63
Issue number1
DOIs
Publication statusPublished - Nov 15 1990

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Hydrides
Hydrogenation
Hydrocarbons
Regioselectivity
Stereochemistry
Catalysts
Isomerization
Alcohols
Temperature
Molecules

ASJC Scopus subject areas

  • Engineering(all)

Cite this

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title = "Low- and high-temperature hydrogenative ring-opening of alkyl-substituted cyclopropanes and methyloxirane over Pd/SiO2 catalyst: detection of β-hydride by a chemical method",
abstract = "The hydrogenative ring-opening of five alkyl-substituted cyclopropanes and of methyl-oxirane on Pd/SiO2 was studied at different temperatures in a closed circulation reactor. For cyclopropanes, the ring opens through simple hydrogenation, giving exclusively saturated hydrocarbons, whereas alcohols (hydrogenation), oxo compounds (isomerization) and also cracking products are produced from methyloxirane. The substituents exert significant effects on the regioselectivity of the reactions for both type of molecules. For the cyclic hydrocarbons, mechanistic pathways are discussed on the basis of the stereochemistry of the compounds and the characteristic features of the ring-opening rate vs. H2-pressure functions. Finally, a chemical method is proposed for the detection of β-hydride.",
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T1 - Low- and high-temperature hydrogenative ring-opening of alkyl-substituted cyclopropanes and methyloxirane over Pd/SiO2 catalyst

T2 - detection of β-hydride by a chemical method

AU - Pálinkó, I.

AU - Notheisz, F.

AU - Bartók, M.

PY - 1990/11/15

Y1 - 1990/11/15

N2 - The hydrogenative ring-opening of five alkyl-substituted cyclopropanes and of methyl-oxirane on Pd/SiO2 was studied at different temperatures in a closed circulation reactor. For cyclopropanes, the ring opens through simple hydrogenation, giving exclusively saturated hydrocarbons, whereas alcohols (hydrogenation), oxo compounds (isomerization) and also cracking products are produced from methyloxirane. The substituents exert significant effects on the regioselectivity of the reactions for both type of molecules. For the cyclic hydrocarbons, mechanistic pathways are discussed on the basis of the stereochemistry of the compounds and the characteristic features of the ring-opening rate vs. H2-pressure functions. Finally, a chemical method is proposed for the detection of β-hydride.

AB - The hydrogenative ring-opening of five alkyl-substituted cyclopropanes and of methyl-oxirane on Pd/SiO2 was studied at different temperatures in a closed circulation reactor. For cyclopropanes, the ring opens through simple hydrogenation, giving exclusively saturated hydrocarbons, whereas alcohols (hydrogenation), oxo compounds (isomerization) and also cracking products are produced from methyloxirane. The substituents exert significant effects on the regioselectivity of the reactions for both type of molecules. For the cyclic hydrocarbons, mechanistic pathways are discussed on the basis of the stereochemistry of the compounds and the characteristic features of the ring-opening rate vs. H2-pressure functions. Finally, a chemical method is proposed for the detection of β-hydride.

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