Bis(cyclooctadiene)nickel(0)

Bis(cyclooctadiene)nickel(0) is the organonickel compound with the formula Ni(C8H12)2, also written Ni(cod)2. It is a diamagnetic coordination complex featuring tetrahedral nickel(0) bound to the alkene groups in two 1,5-cyclooctadiene ligands. This highly air-sensitive yellow solid is a common source of Ni(0) in chemical synthesis.[1]

Bis(cyclooctadiene)nickel(0)
Names
Other names
nickel biscod, Ni(COD)2
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.013.702
EC Number
  • 215-072-0
RTECS number
  • QR6135000
UN number 1325
Properties
C16H24Ni
Molar mass 275.06 g/mol
Appearance Yellow solid
Melting point 60 °C (140 °F; 333 K) (N2, decomposes)
Solubility soluble in benzene, tetrahydrofuran, toluene, diethyl ether, dimethylformamide
Hazards
GHS pictograms
GHS Signal word Danger
H228, H317, H334, H350, H351
P201, P202, P210, P240, P241, P261, P272, P280, P281, P285, P302+352, P304+341, P308+313, P321, P333+313, P342+311, P363, P370+378, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Preparation and properties

The complex is prepared by reduction of anhydrous nickel(II) acetylacetonate in the presence of the diolefin:

Ni(acac)2 + 2 cod + 2 AlEt3 → Ni(cod)2 + 2 acacAlEt2 + C2H6 + C2H4

Ni(cod)2 is moderately soluble in several organic solvents.[2][3] One or both 1,5-cyclooctadiene ligands are readily displaced by phosphines, phosphites, bipyridine, and isocyanides. If exposed to air, the solid oxidizes to nickel(II) oxide.[4] As a result, this compound is generally handled in a glovebox.[5]

References
  1. Wilke, G. (1988). "Contributions to Organo-Nickel Chemistry". Angewandte Chemie International Edition. 27 (1): 185–206. doi:10.1002/anie.198801851.
  2. Schunn, R. A.; Ittel, S. D.; Cushing, M. A. (1990). Bis(1,5-Cyclooctadiene)Nickel(0). Inorganic Syntheses. 28. pp. 94–98. doi:10.1002/9780470132593.ch25. ISBN 978-0-470-13259-3.
  3. Wender, Paul A.; Smith, Thomas E.; Duong, Hung A.; Louie, Janis; Standley, Eric A.; Tasker, Sarah Z. (2015). "Bis(1,5-cyclooctadiene)nickel(0)". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons Ltd: 1–15. doi:10.1002/047084289x.rb118.pub3.
  4. Zhu, Kake; D'Souza, Lawrence; Richards, Ryan M. (September 2005). "Planting of bis(1,5-cyclooctadiene) nickel upon silica to harvest NiO (<5 nm) nanoparticles in a silica matrix". Applied Organometallic Chemistry. 19 (9): 1065–1069. doi:10.1002/aoc.974.
  5. Tasker, Sarah Z.; Standley, Eric A.; Jamison, Timothy F. (2014). "Recent advances in homogeneous nickel catalysis". Nature. 509 (7500): 299–309. doi:10.1038/nature13274. PMC 4344729. PMID 24828188.
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