Bis(1,5-cyclooctadiene)nickel → Nickel

HRID 416669Notes

Reaction equation

HRID 416669 reaction equation
[CH2:1]1[CH2:8][CH:7]=[CH:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[CH2:9]1[CH2:16][CH:15]=[CH:14][CH2:13][CH2:12][CH:11]=[CH:10]1.[Ni:17]>C1(C)C=CC=CC=1>[CH2:8]1[CH2:7][CH:6]=[CH:5][CH2:4][CH2:3][CH:2]=[CH:1]1.[CH2:16]1[CH2:15][CH:14]=[CH:13][CH2:12][CH2:11][CH:10]=[CH:9]1.[Ni:17].[Ni:17]

Participants

4

Reactant 1

HCID 6433264Bis(1,5-cyclooctadiene)nickel2×

Product 2

HCID 935NickelHCID 6433264Bis(1,5-cyclooctadiene)nickel

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

Under an inert atmosphere such as dry nitrogen or argon, a Ni(COD)2 solution is prepared by dissolving Ni(COD)2 (0.065 g) in toluene (2.79 g). A toluene solution, or other appropriate solvent solution, of the multidentate P-containing ligand or a ligand mixture comprising a multidentate P-containing ligand to be tested (0.230 mL of 0.062 mol total multidentate P-containing ligand/L of toluene) is treated with the Ni(COD)2 solution (0.320 mL) and thoroughly mixed to provide a catalyst solution with a zero-valent nickel/multidentate P-containing ligand molar ratio of about 1/1. A cis-2-pentenenitrile (cis-2PN)/HCN/ZnCl2 solution is prepared by combining anhydrous ZnCl2 (0.0406 g), freshly distilled, uninhibited, liquid HCN (0.556 g), and cis-2PN (1.661 g). Into a 2 mL GC vial, a sample of catalyst solution (0.092 mL) is treated with cis-2PN/HCN/ZnCl2 solution (0.034 mL) then the vial is sealed with an aluminum septum cap; the resulting mixture has cis-2PN/nickel molar ratio of about 123, HCN/nickel molar ratio of about 123, and a ZnCl2/nickel molar ratio of about 0.96/1. Over a period of 16 hours, the mixture is heated to about 50° C. The reaction mixture is then cooled to ambient temperature, treated with acetonitrile (0.125 mL), and analyzed by gas chromatography for the amount of ADN, MGN, and 2-ethylsuccinonitrile produced, in order to calculate the percent conversion of 2PN to dinitriles.

Workup

  1. additionP-containing ligand
  2. additionthoroughly mixed

Sources & evidence

ORD record
ord-f73ef01b544843eca1635ca648b7a5d4
Source dataset
uspto-grants-2012_01
Patent number
US08088943B2

Reaction notes

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