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Note | Regular issue | Vol 53, No. 5, 2000, pp.1155-1165
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8829
Transition Metal Complexes of Derivatized Chiral Dihydro-1,2,4-triazin-6-ones. Part I. Nickel(II) Complex of (D)-3-Acetyl-5-benzyl-1-phenyl-4,5-dihydro-1,2,4-triazin-6-one Oxime. An Instance of a Carbon-Carbon Coupling Reaction

Ahmad S. Abushamleh, Mustafa M. El-Abadelah,* and Cäcilia M.-Mössmer

*Chemistry Department, Faculty of Science, University of Jordan, Amman, Jordan

Abstract

The reaction of (D)-3-acetyl-5-benzyl-1-phenyl-4,5-dihydro-1,2,4-triazin-6-one oxime (2) with nickel acetate in refluxing ethanol afforded the respective square planar Ni(II) complex. This is evidenced from an X-Ray study which reveals that the Ni(II) ion is coordinated to the ring N(4) and oxime nitrogen atoms. The crystallographic data of the complex (3) also unravelled that the nickel-complexation has led to the formation of one π-bond across the N(14)-C(15) bond and one σ-bond between a benzylic carbon atom of one ligand and the chiral (C5) carbon atom of the other ligand in the bis-ligand complex (3). Evidently, the complexed Ni(II) ion plays a template effect role in initiating such a cascade of π- and σ-bond forming reactions. 1H-, 13C-NMR and FD-MS spectral data of 3 are in full agreement with its molecular structure.