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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. [11] Famously, cyclopentadiene dimerizes. The conversion occurs in hours at room temperature, but the monomer can be stored for days at ...
Sodium cyclopentadienide is commercially available as a solution in THF.It is prepared by treating cyclopentadiene with sodium: [3]. 2 Na + 2 C 5 H 6 → 2 NaC 5 H 5 + H 2. The conversion can be conducted by heating a suspension of molten sodium in dicyclopentadiene. [2]
Hexachlorocyclopentadiene is prepared by chlorination of cyclopentadiene to give 1,1,2,3,4,5-octachlorocyclopentane, which in a second step undergoes dehydrochlorination: [3] The first procedure uses alkaline hypochlorite and after fractional distillation has a yield of about 75%, the other 25% consists of lower chlorinated cyclopentadienes. [4]
The retro-Diels–Alder reaction is used in the industrial production of cyclopentadiene. Cyclopentadiene is a precursor to various norbornenes, which are common monomers. The Diels–Alder reaction is also employed in the production of vitamin B6. Typical route for production of ethylidene norbornene from cyclopentadiene through vinyl ...
The reaction is reversible and at room temperature cyclopentadiene dimerizes over the course of hours to re-form dicyclopentadiene. Cyclopentadiene is a useful diene in Diels–Alder reactions as well as a precursor to metallocenes in organometallic chemistry. It is not available commercially as the monomer, due to the rapid formation of ...
Cyclopentadienyliron dicarbonyl dimer is an organometallic compound with the formula [(η 5-C 5 H 5)Fe(CO) 2] 2, often abbreviated to Cp 2 Fe 2 (CO) 4, [CpFe(CO) 2] 2 or even Fp 2, with the colloquial name "fip dimer".
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The C 5 O core of the molecule is planar and conjugated, but the bonds have a definite alternating single- and double-bond nature. The C2–C3 and C4–C5 distances are 1.35 Å, while the C1–C2, C3–C4, C5–C1 are closer to single bonds with distances near 1.50 Å. [1]