Ni0-induzierte und -katalysierte Herstellung ungesaettigter Adipinsaeureanilide

Article abstract of DOI:10.1016/0022-328X(91)86489-D

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.