Cyclooctane

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Cyclooctane
Skeletal formula
Names
Preferred IUPAC name
Cyclooctane
Other names
Cyclo-octane
Identifiers
3D model (
JSmol
)
ChEMBL
ChemSpider
ECHA InfoCard
 100.005.484 Edit this at Wikidata
UNII
  • InChI=1S/C8H16/c1-2-4-6-8-7-5-3-1/h1-8H2 checkY
    Key: WJTCGQSWYFHTAC-UHFFFAOYSA-N checkY
  • InChI=1/C8H16/c1-2-4-6-8-7-5-3-1/h1-8H2
    Key: WJTCGQSWYFHTAC-UHFFFAOYAO
  • C1CCCCCCC1
Properties
C8H16
Molar mass 112.21 g/mol
Density 0.834 g/cm3
Melting point 14.59 °C (58.26 °F; 287.74 K)
Boiling point 149 °C (300 °F; 422 K)
7.90 mg/L
−91.4·10−6 cm3/mol
Related compounds
Related cycloalkanes
 Cycloheptane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Cyclooctane is a

molecular formula (CH2)8.[1] It is a simple colourless hydrocarbon
, but it is often a reference compound for saturated eight-membered ring compounds in general.

Cyclooctane has a camphoraceous odor.[2]

Conformations

Further information: Macrocyclic stereocontrol § Cyclooctane

The

conformation of cyclooctane has been studied extensively using computational methods. Hendrickson noted that "cyclooctane is unquestionably the conformationally most complex cycloalkane owing to the existence of many conformers of comparable energy". The boat-chair conformation (below) is the most stable form.[3] This conformation was confirmed by Allinger and co-workers.[4] The crown conformation (below)[5] is slightly less stable. Among the many compounds exhibiting the crown conformation (structure II) is S8, elemental sulfur
.

Boat-chair[6] Crown[6]
Tub[7] Boat-boat[6] Twist boat-chair[6] Twist chair-chair[6]

Synthesis and reactions

The main route to cyclooctane derivatives involves the dimerization of

nickel bis(cyclooctadiene).[8] This process affords, among other products, 1,5-cyclooctadiene (COD), which can be hydrogenated. COD is widely used for the preparation of precatalysts for homogeneous catalysis
. The activation of these catalysts under H2, produces cyclooctane, which is usually discarded or burnt:

C8H12 + 2 H2 → C8H16

Cyclooctane participates in no reactions except those typical of other saturated hydrocarbons,

free radical halogenation. Work in 2009 on alkane functionalisation, using peroxides such as dicumyl peroxide, has opened up the chemistry to some extent, allowing for example the introduction of a phenylamino group.[9]

Amination of cyclooctane by nitrobenzene

References

  1. ISBN 978-1-56670-687-2
    .
  2. PMID 16983730
    .
  3. doi:10.1021/ja01002a036
    .
  4. doi:10.1021/j100248a015
    .
  5. doi:10.1351/goldbook.C01422
  6. ^
    ISSN 0022-3654
    .
  7. S2CID 98272391
    .
  8. doi:10.1002/14356007.a08_205
    .
  9. doi:10.1002/adsc.200800689
    .
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