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trans-Chlorido[6-chloro-4-(4-methoxybenzyl)-3-oxo-3,4-dihydropyrazin-2-yl]bis(triphenylphosphine)palladium(II)
The title compound, [Pd(C(12)H(10)ClN(2)O(2))Cl(C(18)H(15)P)(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 unsatur...
Autores principales: | , , , , |
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Formato: | Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2007
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2914967/ https://www.ncbi.nlm.nih.gov/pubmed/21200660 http://dx.doi.org/10.1107/S1600536807063441 |
Sumario: | The title compound, [Pd(C(12)H(10)ClN(2)O(2))Cl(C(18)H(15)P)(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 Pd(0) to the reactive 3-position of the heterocycle. The coordination around the Pd atom is square planar, with two trans PPh(3) ligands. π–π interactions are observed between the centroid of the pyrazinone ring and planes of two adjacent phenyl rings, one from each PPh(3) 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. |
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