Journal of Organometallic Chemistry p. 403 - 412 (1987)
Update date:2022-08-04
Topics:
Hernandez, Elisa
Hoberg, Heinz
Phenyl isocyanate reacts readily with 1,5-hexadiene and a (ligand)nickel(0) system forming two regioisomeric azanickela-five ring complexes by 1 1 CC-coupling at -10°C. On warming, subsequent reactions eventually yield five-membered carbocyclic amides by intramolecular cyclisation. It has been found that by using a special experimental procedure - continuous slow addition of the isocyanate to a solution containing the diene and nickel(0) complexes - the reaction can be carried out catalytically. With this approach, 1,6-heptadiene gives both a carbocyclic and an acyclic amide. The catalytic cycles are presented and discussed in detail.
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