Cyclooctene is the cycloalkene with a formula C
8H
14. Its molecule has a ring of 8 carbon atoms, connected by seven single bonds and one double bond.
![](http://upload.luquay.com/wikipedia/commons/thumb/5/51/Cyclooctene_Isomers_Structural_Formulae.png/220px-Cyclooctene_Isomers_Structural_Formulae.png)
Cyclooctene is notable because it is the smallest cycloalkene that can exist stably as either the cis or trans stereoisomer, with cis-cyclooctene being the most common. Theoretical analysis implies a total of 16 conformational and configurational isomers, all chiral, forming 8 enantiomeric pairs.[1] The cis isomer can adopt various conformations, the most stable one being shaped like a ribbon.[1] The most stable conformation of trans-cyclooctene is shaped like the 8-carbon equivalent of the chair conformation of cyclohexane.
Longer cycloalkene rings such as the ten-carbon cyclodecene also occur as cis and trans isomers.
References
edit- ^ a b 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.
External links
edit- Media related to Cyclooctene at Wikimedia Commons