|CAS number||, (Z,Z), (Z,E), (E,E)|
|PubChem||, (Z,Z), (Z,E), (E,E)|
|ChemSpider||, (Z,Z) , (Z,E) , (E,E)|
|Jmol-3D images||Image 1|
|Molar mass||108.18 g mol−1|
|Melting point||−69 °C; −92 °F; 204 K|
|Boiling point||150 °C; 302 °F; 423 K|
|Vapor pressure||910 Pa|
|Refractive index (nD)||1.493|
heat capacity C
|198.9 J K-1 mol-1|
|250.0 J K-1 mol-1|
|Std enthalpy of
|21-27 kJ mol-1|
|Std enthalpy of
|-4.890--4.884 MJ mol-1|
|GHS signal word||DANGER|
|GHS hazard statements||H226, H304, H315, H317, H319, H334|
|GHS precautionary statements||P261, P280, P301+310, P305+351+338, P331, P342+311|
|R-phrases||R10, R36/38, R42/43, R65|
|S-phrases||S23, S26, S36/37, S62|
|Flash point||32–38 °C|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
1,5-Cyclooctadiene is the organic compound with the chemical formula C8H12. Generally abbreviated COD, this diene is a useful precursor to other organic compounds and serves as a ligand in organometallic chemistry.
COD adds SCl2 (or similar reagents) to give 2,6-dichloro-9-thiabicyclo[3.3.1]nonane:
1,5-COD typically binds to low-valent metals via both alkene groups. The complex Ni(COD)2 is a precursor to several nickel(0) and Ni(II) complexes. Metal-COD complexes are attractive because they are sufficiently stable to be isolated, often being more robust than related ethylene complexes. The stability of COD complexes is attributable to the chelate effect. The COD ligands are easily displaced by other ligands, such as phosphines.
- 1/3 [Ni(C5H7O2)2]3 + 2 COD + 2 Al(C2H5)3 → Ni(COD)2 + 2 Al(C2H5)2(C5H7O2) + C2H4 + C2H6
- Li2C8H8 + PtCl2(COD) + 3 C7H10 → [Pt(C7H10)3] + 2 LiCl + C8H8 + C8H12
- Pt(C7H10)3 + 2 COD → Pt(COD)2 + 3 C7H10
Extensive work has been reported on complexes of COD, much of which can has been described in volumes 25, 26, and 28 of Inorganic Syntheses. The platinum complex has been used in many syntheses:
- Pt(COD)2 + 3 C2H4 → Pt(C2H4)3 + 2 COD
COD complexes are useful as starting materials, one noteworthy example is the reaction:
- Ni(COD)2 + 4 CO(g) Ni(CO)4 + 2 COD
The product Ni(CO)4 is highly toxic, thus it is advantageous to generate it in the reaction vessel as opposed to being dispensed directly. Other low-valent metal complexes of COD include Mo(COD)(CO)4, [RuCl2(COD)]n, and Fe(COD)(CO)3. COD is an especially important in the coordination chemistry of rhodium(I) and iridium(I), examples being Crabtree's catalyst and cyclooctadiene rhodium chloride dimer.
The highly strained trans-trans isomer of 1,5-cyclooctadiene is a known compound. (E,E)-COD was first synthesized by Whitesides and Cope in 1969 by photoisomerization of the cis compound. Another synthesis (double elimination reaction from a cyclooctane ring) was reported by Huisgen in 1987. The molecular conformation of (E,E)-COD is twisted rather than chair-like. The compound has been investigated as a click chemistry mediator.
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