{{Short description|Chemical compound}} thumb|Possible isomers of cyclooctene.'''Cyclooctene''' is the cycloalkene with a formula {{chem|C|8|H|14}}. Its molecule has a ring of 8 carbon atoms, connected by seven single bonds and one double bond.
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.<ref name=neue2011/> The ''cis'' isomer can adopt various conformations, the most stable one being shaped like a ribbon.<ref name=neue2011>{{cite journal |first1= Ulrich |last1= Neuenschwander |first2= Ive |last2= Hermans |doi= 10.1021/jo202176j |title= The conformations of cyclooctene: Consequences for epoxidation chemistry |journal= J. Org. Chem. |volume= 76 |issue= 24 |pages= 10236–10240 |year= 2011 |pmid= 22077196 }}</ref> 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== {{Reflist}}
==External links== *{{Commonscatinline}}
Category:Cycloalkenes Category:Eight-membered rings