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Concept
Cyclopentadiene
Summary
Cyclopentadiene is an organic compound with the formula C5H6. It is often abbreviated CpH because the cyclopentadienyl anion is abbreviated Cp−.
This colorless liquid has a strong and unpleasant odor. At room temperature, this cyclic diene dimerizes over the course of hours to give dicyclopentadiene via a Diels–Alder reaction. This dimer can be restored by heating to give the monomer.
The compound is mainly used for the production of cyclopentene and its derivatives. It is popularly used as a precursor to the cyclopentadienyl anion (Cp−), an important ligand in cyclopentadienyl complexes in organometallic chemistry.
Cyclopentadiene production is usually not distinguished from dicyclopentadiene since they interconvert. They are obtained from coal tar (about 10–20 g/tonne) and by steam cracking of naphtha (about 14 kg/tonne). To obtain cyclopentadiene monomer, commercial dicyclopentadiene is cracked by heating to around 180 °C. The monomer is collected by distillation, and used soon thereafter. It advisable to use some form of fractionating column when doing this, to remove refluxing uncracked dimer.
The hydrogen atoms in cyclopentadiene undergo rapid [1,5]-sigmatropic shifts. The hydride shift is however sufficiently slow at 0 °C to allow alkylated derivatives to be manipulated selectively.
Even more fluxional are the derivatives C5H5E(CH3)3 (E = Si, Ge, Sn), wherein the heavier element migrates from carbon to carbon with a low activation barrier.
Cyclopentadiene is a highly reactive diene in the Diels–Alder reaction because minimal distortion of the diene is required to achieve the envelope geometry of the transition state compared to other dienes. Famously, cyclopentadiene dimerizes. The conversion occurs in hours at room temperature, but the monomer can be stored for days at −20 °C.
Cyclopentadienyl anion
The compound is unusually acidic (pKa = 16) for a hydrocarbon, a fact explained by the high stability of the aromatic cyclopentadienyl anion, C5H5−. Deprotonation can be achieved with a variety of bases, typically sodium hydride, sodium metal, and butyl lithium.
Official source
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