Cyclooctene

Cyclooctene is the cycloalkene with an formula C
₈H
₁₄. Its molecule has a ring of 8 carbon atoms, connected by seven single bonds and one double bond.

Possible isomers of cyclooctene.

Cyclooctene is notable because it is the smallest cycloalkene that can exist as either the cis- or trans-isomer, with the cis-isomer being more common. Theoretical analyisis implies a total of 16 conformational and configurational isomers, all chiral, forming 8 enantiomer pairs.[1] Its most stable cis stereoisomer can adopt various conformations, the most stable one being shaped like a ribbon;[1]

The most stable trans-conformer is shaped like the 8-carbon equivalent chair conformation of cyclohexane.

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.

External links

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[neue2011-1] Neuenschwander, Ulrich; Hermans, Ive (2011). "The conformations of cyclooctene: Consequences for epoxidation chemistry". J. Org. Chem. 76 (24): 10236–10240. doi:10.1021/jo202176j.