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
3D model (JSmol)
ChemSpider
  • InChI=1S/2C3H5.Ni/c2*1-3-2;/h2*3H,1-2H2;/q2*-1;+2
    Key: CXZRBHUCODWFTL-UHFFFAOYSA-N
  • [CH2-]C=C.[CH2-]C=C.[Ni+2]
Properties
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).

Preparation and reactions

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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

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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.