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Cyclopentene
Organic compound; 5-sided hydrocarbon ring From Wikipedia, the free encyclopedia
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Cyclopentene is a chemical compound with the formula (CH2)3(CH)2. It is a colorless liquid with a petrol-like odor. It has few applications, and thus is mainly used as a minor component of gasoline, present in concentrations of less than 1%.[1][2] It is one of the principal cycloalkenes.
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History and synthesis
Cyclopentene was first prepared by Carl Gärtner in 1893 from iodocyclopentane with potassium hydroxide. He named it pentamethenylene (German: Pentamethenylen).[3]
Cyclopentene is produced industrially in large amounts by steam cracking of naphtha. In the laboratory, it is prepared by dehydration of cyclopentanol.[4] Substituted cyclopentenes are the product of the vinylcyclopropane-cyclopentene rearrangement.[5]
It can also be produced by the catalytic hydrogenation of cyclopentadiene.[6]
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The polymerization of cyclopentene by Ziegler-Natta catalysts yields 1,3-linkages, not the more typical 1,2-linked polymer.[7]
Palladium-catalyzed hydrocarboxylation of cyclopentene gives cyclopentanecarboxylic acid:[8]
- C5H8 + CO + H2O → C5H9CO2H
References
External links
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