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-cyclooctadieneligands. This highly air-sensitive yellow solid is a common source of Ni(0) in chemical synthesis.[1]
Preparation and properties
The complex is prepared by reduction of anhydrous
nickel(II) acetylacetonate in the presence of the diolefin:
Ni(cod)2 is moderately soluble in several organic solvents.[2][3]
If exposed to air, the solid oxidizes in a few minutes to
nickel(II) oxide.[4] As a result, this compound is generally handled in a
glovebox.[5]
Reactions
The reactivity of Ni(cod)2 has been extensively examined. One or both
1,5-cyclooctadiene ligands are readily displaced by phosphines, phosphites,
bipyridine, and
isocyanides. [6]
^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.
ISBN9780470842898.
^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.