Summary
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1.
The presence of palladium the triple C ≡ C bond in di-2-cyclopenten-1-ylacetylene is selectively hydrogenated to a double bond.
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2.
In presence of platinum, after the addition of three molecular proportions of hydrogen to di-2-cyclopenten-1-ylacetylene 1,2-dicyclopentylethylene is formed, i.e., the double bonds in the five-membered rings are preferentially hydrogenated.
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3.
In presence of palladium, as a result of the isomerizing action of this catalyst, the addition of three molecular proportions of hydrogen to di-2-cyclopenten-1-ylacetylene results in the formation of a mixture of unsaturated hydrocarbons, in which 1,2-dicyclopentylethylene and 1-(1-cyclopenten-1-yl)-2-cyclopentylethane predominate.
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4.
The preferential addition of hydrogen at the double bond in the five-membered ring rather than at the double bond in the open chain is observed also in the partial hydrogenation (to the extent of 50%) of an equimolecular mixture of 3-methylcyclopentene and 2-octene over platinum black.
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Platé, A.F., Stanko, V.I. Hydrogenation of di-2-cyclopenten-1-ylacetylene over Pd, Pt, and Ni catalysts. Russ Chem Bull 9, 1375–1382 (1960). https://doi.org/10.1007/BF00907672
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DOI: https://doi.org/10.1007/BF00907672