Cyclopentadiene

Cyclopentadiene is an organic compound made of carbon and hydrogen. It has the chemical formula C₅H₆.

Uses

Cyclopentadiene's two double bonds are held on the same side of the single bond between them by the cycle structure. This shape is very close to the shape needed for the Diels-Alder reaction. It is much easier for cyclopentadiene to go through this reaction than other dienes.^[1] It reacts with ethylene to make norbornene, and with other alkenes to make substituted norbornenes like vinyl norbornene (from butadiene).

Cyclopentadiene is a very weak acid. It reacts with strong bases to make the aromatic cyclopentadienide anion.^[2] Sodium cyclopentadienide is an important ingredient in making metallocenes, a class of organometallic compounds used as catalysts.

References

↑ Levandowski, Brian J.; Raines, Ronald T. (2021). "Click Chemistry with Cyclopentadiene". Chemical Reviews. 121 (12): 6777–6801. doi:10.1021/acs.chemrev.0c01055. PMID 33651602.
↑ US patent 8057714, Yong Gyu Han, Ki-Soo Lee, Heon-Yong Kwon, Jong-Sang Park, Nicola Maggiarosa, "Synthesis method of metal cyclopentadienide in bulk", issued 2011-11-15, assigned to LG Chemical Ltd

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[1] Levandowski, Brian J.; Raines, Ronald T. (2021). "Click Chemistry with Cyclopentadiene". Chemical Reviews. 121 (12): 6777–6801. doi:10.1021/acs.chemrev.0c01055. PMID 33651602.

[2] US patent 8057714, Yong Gyu Han, Ki-Soo Lee, Heon-Yong Kwon, Jong-Sang Park, Nicola Maggiarosa, "Synthesis method of metal cyclopentadienide in bulk", issued 2011-11-15, assigned to LG Chemical Ltd

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