Cyclooctene
Cycloocteneis thecycloalkenewith a formulaC
8H
14.Its molecule has a ring of 8carbonatoms, connected by sevensingle bondsand onedouble bond.
Cyclooctene is notable because it is the smallest cycloalkene that can exist stably as either thecisortransstereoisomer,withcis-cyclooctenebeing the most common. Theoretical analysis implies a total of 16conformationalandconfigurationalisomers, all chiral, forming 8enantiomericpairs.[1]Thecisisomer can adopt various conformations, the most stable one being shaped like a ribbon.[1]The most stable conformation oftrans-cycloocteneis shaped like the 8-carbon equivalent of the chair conformation ofcyclohexane.
Longer cycloalkene rings such as the ten-carboncyclodecenealso occur ascisandtransisomers.
References
[edit]- ^abNeuenschwander, Ulrich; Hermans, Ive (2011). "The conformations of cyclooctene: Consequences for epoxidation chemistry".J. Org. Chem.76(24): 10236–10240.doi:10.1021/jo202176j.PMID22077196.
External links
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