Bis(allyl)nickel

Bis(allyl)nickel
Names
	IUPAC name Bis(π‐allyl)nickel(II)
	Other names diallylnickel
Identifiers
CAS Number	12077-85-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	17218878;
PubChem CID	12494635;
	InChI InChI=1S/2C3H5.Ni/c21-3-2;/h23H,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

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.

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

References

Goddard, R.; Krueger, C.; Mark, F.; Stansfield, R.; Zhang, X. (1985). "Effect upon the Hydrogen Atoms of Bonding an Allyl Group to a Transition Metal. A Theoretical Investigation and an Experimental Determination using Neutron Diffraction of the Structure of Bis(η³-allyl)nickel". Organometallics. 4 (2): 285–290. doi:10.1021/om00121a014.
O'Brien, S.; Fishwick, M.; McDermott, B.; Wallbridge, M. G. H.; Wright, G. A. (1972). "Isoleptic Allyl Derivatives of Various Metals". Inorganic Syntheses. Inorganic Syntheses. Vol. 13. pp. 73–79. doi:10.1002/9780470132449.ch14. ISBN 9780470132449.
Wilke, G.; Bogdanovič, B. (1961). "Bis-π-allyl-nickel". Angewandte Chemie. 73 (23): 756. Bibcode:1961AngCh..73..756W. doi:10.1002/ange.19610732306.
Henc, B.; Jolly, P.W.; Salz, R.; Stobbe, S.; Wilke, G.; Benn, R.; Mynott, R.; Seevogel, K.; Goddard, R.; Krüger, C. (1980). "Transition metal allyls". Journal of Organometallic Chemistry. 191 (2): 449–475. doi:10.1016/S0022-328X(00)81073-6.

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[1] Goddard, R.; Krueger, C.; Mark, F.; Stansfield, R.; Zhang, X. (1985). "Effect upon the Hydrogen Atoms of Bonding an Allyl Group to a Transition Metal. A Theoretical Investigation and an Experimental Determination using Neutron Diffraction of the Structure of Bis(η³-allyl)nickel". Organometallics. 4 (2): 285–290. doi:10.1021/om00121a014.

[2] O'Brien, S.; Fishwick, M.; McDermott, B.; Wallbridge, M. G. H.; Wright, G. A. (1972). "Isoleptic Allyl Derivatives of Various Metals". Inorganic Syntheses. Inorganic Syntheses. Vol. 13. pp. 73–79. doi:10.1002/9780470132449.ch14. ISBN 9780470132449.

[3] Wilke, G.; Bogdanovič, B. (1961). "Bis-π-allyl-nickel". Angewandte Chemie. 73 (23): 756. Bibcode:1961AngCh..73..756W. doi:10.1002/ange.19610732306.

[4] Henc, B.; Jolly, P.W.; Salz, R.; Stobbe, S.; Wilke, G.; Benn, R.; Mynott, R.; Seevogel, K.; Goddard, R.; Krüger, C. (1980). "Transition metal allyls". Journal of Organometallic Chemistry. 191 (2): 449–475. doi:10.1016/S0022-328X(00)81073-6.