Bis(1,5-cyclooctadiene)nickel → Nickel
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
Reactant 1
Product 2
Reagents, catalysts & solvents 1
Procedure
Under an inert atmosphere such as dry nitrogen or argon, a Ni(COD)2 solution is prepared by dissolving Ni(COD)2 (0.039 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 precursor solution with a zero-valent nickel/multidentate P-containing ligand molar ratio of about 1/1. A cis-2-pentenenitrile (cis-2PN)/ZnCl2 solution is prepared by dissolving ZnCl2 (0.017 g in 1.02 g cis-2PN). A sample of catalyst precursor solution (0.100 mL) is treated with cis-2PN/ZnCl2 solution (0.025 mL); the resulting mixture has cis-2PN/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 0C and exposed to HCN vapor supplied from a reservoir of uninhibited, liquid HCN at ambient temperature (619 mm Hg or 82.5 kPa vapor pressure at 20 0C). 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
- additionP-containing ligand
- additionthoroughly mixed
Sources & evidence
- ORD record
- ord-4bbf2546eb6c48ae9c7eeb8a79f59944
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07709674B2
Reaction notes
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