Bis(allyl)nickel

Bis(allyl)nickel is an organonickel compound with the formula Ni(η³-C₃H₅)₂. The molecule consists of two allyl ligands bound to nickel(II). It has inversion symmetry.^[1] It is a volatile yellow liquid at room temperature.

Bis(allyl)nickel

Names
IUPAC name Bis(π‐allyl)nickel(II)
Other names diallylnickel
Identifiers
CAS Number	12077-85-9 Y
3D model (JSmol)	Interactive image
ChemSpider	17218878
PubChem CID	12494635
InChI InChI=1S/2C3H5.Ni/c2*1-3-2;/h2*3H,1-2H2;/q2*-1;+2 Key: CXZRBHUCODWFTL-UHFFFAOYSA-N
SMILES [CH2-]C=C.[CH2-]C=C.[Ni+2]
Properties
Chemical formula	C6H10Ni
Molar mass	140.839 g·mol−1
Appearance	yellow liquid
Density	1.537 g/cm3
Melting point	0 °C (32 °F; 273 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Preparation and reactions

It can be prepared by the reaction of allyl magnesium bromide with anhydrous nickel chloride.^[2] It was first prepared similarly by Gunther Wilke et al. The same group reported that the complex react with carbon monoxide to give nickel tetracarbonyl and 1,5-hexadiene. It catalyzes the trimerization of butadiene.^[3] With tertiary phosphines, the complex gives the tetrakis derivative. Such reactions to proceed via the intermediacy of the 18-electron adduct.^[4]

Ni(C₃H₅)₂ + PR₃ → Ni(C₃H₅)₂(PR₃)

Ni(C₃H₅)₂PR₃ → Ni(CH₂=CHCH₂CH₂CH=CH₂)(PR₃)

Ni(CH₂=CHCH₂CH₂CH=CH₂)(PR₃) + 3 PR₃ → Ni(PR₃)₄ + CH₂=CHCH₂CH₂CH=CH₂