cis-Cyclooctene is a cycloalkene with the formula (CH2)6(CH)2. It is a colorless liquid that is used industrially to produce a polymer. It is also a ligand in organometallic chemistry.
Cyclooctene is the smallest cycloalkene that can be isolated as both the cis- and trans-isomer. cis-Cyclooctene is shaped like the 8-carbon equivalent chair conformation of cyclohexane.
| cis-Cyclooctenein chair conformation | (Rp)-trans-Cyclooctenein crown conformation |
Uses and reactions
Cyclooctene undergoes ring-opening metathesis polymerization to give polyoctenamers, which are marketed under the name Vestenamer.2
cis-Cyclooctene (COE) is a substrate known for quite selectively forming the epoxide, as compared to other cycloalkenes, e.g. cyclohexene. Low amounts of radical by-products are found only. This behaviour is attributed to the difficulty of functionalizing allylic CH centers, which almost orthogonal allylic C-H bonds. Therefore, if radicals are around, they tend to form epoxide via an addition-elimination mechanism.3
It is used as an easily displaced ligand in organometallic chemistry, e.g. chlorobis(cyclooctene)rhodium dimer and chlorobis(cyclooctene)iridium dimer.
References
Neuenschwander, Ulrich; Hermans, Ive (2011). "The Conformations of Cyclooctene: Consequences for Epoxidation Chemistry". J. Org. Chem. 76 (24): 10236–10240. doi:10.1021/jo202176j. PMID 22077196. /wiki/J._Org._Chem. ↩
Lionel Delaude; Alfred F. Noels (2005). "Metathesis". Kirk-Othmer Encyclopedia of Chemical Technology. Weinheim: Wiley-VCH. doi:10.1002/0471238961.metanoel.a01. ISBN 0471238961. 0471238961 ↩
Neuenschwander, Ulrich; Hermans, Ive (2011). "The Conformations of Cyclooctene: Consequences for Epoxidation Chemistry". J. Org. Chem. 76 (24): 10236–10240. doi:10.1021/jo202176j. PMID 22077196. /wiki/J._Org._Chem. ↩