Cyclopentadiene Hydrogenation
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Cyclopentadiene Hydrogenation
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. Production and reactions Cyclopentadiene production is usually not distinguished from dicyclopentadiene since they interconvert. They are obtained from coal tar (about 10–20 g/ t) and by steam cracking of naphtha (about 14 kg/t). To obtain cyclopentadiene monomer, commercial dicyclopentadiene is cracked by heating to around 180 °C. ...
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Terpene
Terpenes () are a class of natural products consisting of compounds with the formula (C5H8)n for n ≥ 2. Terpenes are major biosynthetic building blocks. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants, particularly Pinophyta, conifers. In plants, terpenes and terpenoids are important mediators of ecological biological interaction, interactions, while some insects use some terpenes as a form of defense. Other functions of terpenoids include cell growth modulation and plant elongation, light harvesting and photoprotection, and membrane permeability and fluidity control. Terpenes are classified by the number of carbons: monoterpenes (C10), sesquiterpenes (C15), diterpenes (C20), as examples. The terpene alpha-pinene is a major component of the common solvent, turpentine. The one terpene that has major applications is natural rubber (i.e., polyisoprene). The possibility that other terpenes could be used as precursors to pr ...
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Retro-Diels–Alder Reaction
The retro-Diels–Alder reaction (rDA reaction) is the reverse of the Diels–Alder reaction, Diels–Alder (DA) reaction, a [4+2] cycloelimination. It involves the formation of a diene and dienophile from a cyclohexene. It can be accomplished spontaneously with heat, or with acid or base mediation. In principle, it becomes thermodynamically favorable for the Diels–Alder reactions to proceed in the reverse direction if the temperature is high enough. In practice, this reaction generally requires some special structural features in order to proceed at temperatures of synthetic relevance. For instance, the cleavage of cyclohexene to give butadiene and ethene has been observed, but only at temperatures exceeding 800 K. With an appropriate driving force, however, the Diels–Alder reaction proceeds in reverse under relatively mild conditions, providing diene and dienophile from starting cyclohexene derivatives. As early as 1929, this process was known and applied to the detection of ...
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