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cis-Cyclooctene

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cis-Cyclooctene[1]
Names
Preferred IUPAC name
(Z)-Cyclooctene
Other names
cis-Cyclooctene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.012.040 Edit this at Wikidata
EC Number
  • 213-243-4
UNII
  • InChI=1S/C8H14/c1-2-4-6-8-7-5-3-1/h1-2H,3-8H2/b2-1-
    Key: URYYVOIYTNXXBN-UPHRSURJSA-N
  • InChI=1/C8H14/c1-2-4-6-8-7-5-3-1/h1-2H,3-8H2/b2-1-
    Key: URYYVOIYTNXXBN-UPHRSURJBT
  • C\1=C\CCCCCC/1
Properties
C8H14
Molar mass 110.200 g·mol−1
Density 0.846 g/mL
Melting point −16 °C (3 °F; 257 K)
Boiling point 145 to 146 °C (293 to 295 °F; 418 to 419 K)
Hazards
GHS labelling:
GHS02: FlammableGHS08: Health hazard
Danger
H226, H304
P210, P233, P240, P241, P242, P243, P280, P301+P310, P303+P361+P353, P331, P370+P378, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

cis-Cyclooctene is a cycloalkene with the formula (CH2)6(CH)2. It is a colorless liquid that is used industrially to produce a polymer. It is also a ligand in organometallic chemistry.

Cyclooctene is the smallest cycloalkene that can be isolated as both the cis- and trans-isomer.[2] cis-Cyclooctene is shaped like the 8-carbon equivalent chair conformation of cyclohexane.

cis-Cyclooctene
in chair conformation		 (Rp)-trans-Cyclooctene
in crown conformation

Uses and reactions

Cyclooctene undergoes ring-opening metathesis polymerization to give polyoctenamers, which are marketed under the name Vestenamer.[3]

cis-Cyclooctene (COE) is a substrate known for quite selectively forming the epoxide, as compared to other cycloalkenes, e.g. cyclohexene. Low amounts of radical by-products are found only. This behaviour is attributed to the difficulty of functionalizing allylic CH centers, which almost orthogonal allylic C-H bonds. Therefore, if radicals are around, they tend to form epoxide via an addition-elimination mechanism.[2]

It is used as an easily displaced ligand in organometallic chemistry, e.g. chlorobis(cyclooctene)rhodium dimer and chlorobis(cyclooctene)iridium dimer.

References

  1. ^ "cis-Cyclooctene". Sigma-Aldrich.
  2. ^ 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.
  3. ^ Lionel Delaude; Alfred F. Noels (2005). "Metathesis". Kirk-Othmer Encyclopedia of Chemical Technology. Weinheim: Wiley-VCH. doi:10.1002/0471238961.metanoel.a01. ISBN 0471238961.
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