Bis(cyclooctadiene)nickel(0)

Bis(cyclooctadiene)nickel(0)
Names
	Other names nickel biscod
Identifiers
CAS Number	1295-35-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	17215769 ;
ECHA InfoCard	100.013.702
PubChem CID	6433264;
RTECS number	QR6135000;
CompTox Dashboard (EPA)	DTXSID2024614 ;
	InChI InChI=1S/2C8H8.Ni/c21-2-4-6-8-7-5-3-1;/h21-2,7-8H2; Key: AYHVBQBQROAZHP-UHFFFAOYSA-N ; InChI=1/2C8H8.Ni/c21-2-4-6-8-7-5-3-1;/h21-2,7-8H2; Key: AYHVBQBQROAZHP-UHFFFAOYAH;
	SMILES C1C[C][C]CC[C][C]1.C1C[C][C]CC[C][C]1.[Ni];
Properties
Chemical formula	C16H24Ni
Molar mass	275.06 g/mol
Appearance	Yellow solid
Melting point	60 °C (140 °F; 333 K) (decomposes)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Bis(cyclooctadiene)nickel(0) is the organometallic compound with the formula Ni(C₈H₁₂)₂. This air-sensitive yellow solid is a common source of Ni(0) in chemical synthesis.^[1]

Ni(cod)₂, as it is commonly abbreviated, is a diamagnetic coordination complex featuring tetrahedral nickel(0) bound to the alkene groups in two 1,5-cyclooctadiene ligands. The complex is prepared by reduction of anhydrous nickel(II) acetylacetonate in the presence of the diolefin:

1/3 [Ni₃(acac)₆] + 2 cod + 2 AlEt₃ → Ni(cod)₂ + 2 acacAlEt₂ + C₂H₆ + C₂H₄

Ni(cod)₂ is moderately soluble in benzene and THF.^[2] The cod ligands are easily displaced by phosphines, phosphites, and isocyanides.

References

^ Wilke, G. (1988). "Contributions to Organo-Nickel Chemistry". Angewandte Chemie International Edition. 27 (1): 185–206. doi:10.1002/anie.198801851.
^ Schunn, R. A.; Ittel, S. D.; Cushing, M. A. (1990). "Bis(1,5-Cyclooctadiene)Nickel(0)". Inorganic Syntheses. 28: 94–98. doi:10.1002/9780470132593.ch25. ISBN 978-0-470-13259-3.

[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: 94–98. doi:10.1002/9780470132593.ch25. ISBN 978-0-470-13259-3.

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