Bis(cyclooctadiene)nickel(0)

Bis(cyclooctadiene)nickel(0)
Other names nickel biscod
Identifiers
CAS number	1295-35-8 Y
ChemSpider	17215769 Y
RTECS number	QR6135000
Jmol-3D images	Image 1
SMILES C1C[C][C]CC[C][C]1.C1C[C][C]CC[C][C]1.[Ni]
InChI InChI=1S/2C8H8.Ni/c2*1-2-4-6-8-7-5-3-1;/h2*1-2,7-8H2; Y Key: AYHVBQBQROAZHP-UHFFFAOYSA-N Y InChI=1/2C8H8.Ni/c2*1-2-4-6-8-7-5-3-1;/h2*1-2,7-8H2; Key: AYHVBQBQROAZHP-UHFFFAOYAH
Properties
Molecular formula	C16H24Ni
Molar mass	275.06 g/mol
Appearance	Yellow solid
Melting point	60 °C with decomp.
Hazards
R-phrases	Template:R11-40
S-phrases	S36/37
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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

1. ^ Günther Wilke (1988). "Contributions to Organo-Nickel Chemistry". Angewandte Chemie International Edition in English 27: 185–206. doi:10.1002/anie.198801851. 
2. ^ R. A. Schunn, S. D. Ittel, and M. A. Cushing (1990). "Bis(cyclooctadiene)nickel". Inorg. Synth.. Inorganic Syntheses 28: 94–98. doi:10.1002/9780470132593.ch25. ISBN 9780470132593.