Acta Cryst. (2008). E64, m93  [ doi:10.1107/S1600536807063441 ]

trans-Chlorido[6-chloro-4-(4-methoxybenzyl)-3-oxo-3,4-dihydropyrazin-2-yl]bis(triphenylphosphine)palladium(II)

K. Robeyns, J. Alen, W. M. De Borggraeve, F. Compernolle and L. Van Meervelt

Abstract: The title compound, [Pd(C₁₂H₁₀ClN₂O₂)Cl(C₁₈H₁₅P)₂], is the intermediate of the reduction of a 3,5-dichloropyrazinone [Loosen, Tutonda, Khorasani, Compernolle & Hoornaert (1991). Tetrahedron, 47, 9259-9268]. This species is formed by oxidative addition of coordinatively unsaturated Pd⁰ to the reactive 3-position of the heterocycle. The coordination around the Pd atom is square planar, with two trans PPh₃ ligands. - interactions are observed between the centroid of the pyrazinone ring and planes of two adjacent phenyl rings, one from each PPh₃ group (3.25 and 3.078 Å), stabilizing the intermediate structure. This could explain the reduced reactivity towards substitution of the Cl atom by the formate anion, resulting in poor yield of the reduced compound. 3-Substituted pyrazinones are important precursors in the synthesis of 5-aminopiperidinone-2-carboxylate (APC) systems.

Online 6 December 2007

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