Stoichiometric Schiff base condensations of sterically bulky primary amines with acenaphthenequinone yield isolable monoimines. In the presence of iron(II) chloride, the remaining ketone reacts with a second primary amine bearing a pendant donor atom to give asymmetric, tridentate, R-diimine complexes that possess remarkable structural variability. A series of NNP and NNS tridentate iron(II) complexes are prepared; these coordination compounds become active catalysts for ethylene oligomerization when activated with methylalumoxanes. X-ray crystallographic studies of the precatalyst complexes confirm that the ligand binds in a tridentate fashion. Correlations between the precatalyst solid-state structures and catalyst activity and R-olefin product distribution are explored.
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