Cyclooctene is a cycloalkene with an eight-membered ring. It is notable because it is the smallest cycloalkene that can exist as either the cis- or trans-isomer with the cis-isomer more common. Its most stable cis stereoisomer can adopt various conformations, the most stable one being shaped like a ribbon;[1] its most stable trans-conformer is shaped like the 8-carbon equivalent chair conformation of cyclohexane.


  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.
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