Journal of Organometallic Chemistry p. 401 - 409 (1991)
Update date:2022-08-02
Topics:
Hoberg, Heinz
Baerhausen, Dieter
It is shown that 4-pentencarboxylic acid anilide (I), which can readily be prepared catalytically from ethene and phenyl isocyanate (II), further reacts with II on ligand-nickel(0)-systems in a highly regioselective reaction to form triphenylphosphine-5-azanickelacyclopentan-4-one (Va).Protonolysis of Va leads to adipic acid anilide.When Va is treated with maleic acid anhydride at 20 deg C. a β'-H-elimination, is induced because the hydrolysis gives the symmetric 3-hexendicarboxylic acid dianilide (XII) with high selectivity.The catalytic reaction of I and II on a ligand-nickel(0)-complex (ligand = tricyclohexyl-phosphite) involves a β-H-elimination to yield 2-hexendicarboxylic acid dianilide (XI).This opens up the possibility of producing adipic acid derivatives catalytically in a two step synthesis from ethene and phenyl isocyanate.The mechanisms and special features are discussed.
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