Organonickel chemistry

In solution however solvent always interact with the metal atom increasing the electron count.

One 12 VE compound is di(mesityl)nickel prepared from (allyl)2Ni2Br2 and the corresponding Grignard reagent.

Practical applications of this theme include polymerization or oligomerization of alkenes, as in the Shell Higher Olefin Process.

Nickelocene NiCp2 with +2 Ni oxidation state and 20 valence electrons is the main metallocene of nickel.

[10] Benzyne is generated in situ from a benzene compound attached to a triflate and a trimethylsilyl substituent in the ortho- positions and reacts with a di-yne such as 1,7-octadiyne along with a nickel(II) bromide / zinc catalyst system (NiBr2 bis(diphenylphosphino) ethane / Zn) to synthesize the corresponding naphthalene derivative.

A cyclometalation step follows to the nickelcyclopentadiene intermediate and then coordination of the benzyne which gives a C-H insertion reaction to the nickelcycloheptatriene compound.

The formation of organonickel compounds in this type of reaction is not always obvious but in a carefully designed experiment two such intermediates are formed quantitatively:[11][12] It is noted in one study [13] that this reaction only works with acetylene itself or with simple alkynes due to poor regioselectivity.

One strategy to remedy this problem employs certain diynes: The selected reaction conditions also minimize the amount formed of competing [2+2+2]cycloaddition product to the corresponding substituted arene.

The industrial production of acrylic acid at one time consisted of combining acetylene, carbon monoxide and water at 40-55 atm and 160-200 °C with nickel(II) bromide and a copper halide.