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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...

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Detalles Bibliográficos
Autores principales: Robeyns, Koen, Alen, Jo, De Borggraeve, Wim M., Compernolle, Frans, Van Meervelt, Luc
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2007
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
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author Robeyns, Koen
Alen, Jo
De Borggraeve, Wim M.
Compernolle, Frans
Van Meervelt, Luc
author_facet Robeyns, Koen
Alen, Jo
De Borggraeve, Wim M.
Compernolle, Frans
Van Meervelt, Luc
author_sort Robeyns, Koen
collection PubMed
description 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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spelling pubmed-29149672010-12-30 trans-Chlorido[6-chloro-4-(4-methoxy­benz­yl)-3-oxo-3,4-dihydro­pyrazin-2-yl]­bis­(triphenyl­phosphine)palladium(II) Robeyns, Koen Alen, Jo De Borggraeve, Wim M. Compernolle, Frans Van Meervelt, Luc Acta Crystallogr Sect E Struct Rep Online Metal-Organic Papers 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. International Union of Crystallography 2007-12-06 /pmc/articles/PMC2914967/ /pubmed/21200660 http://dx.doi.org/10.1107/S1600536807063441 Text en © International Union of Crystallography 2008 http://journals.iucr.org/services/termsofuse.html This is an open-access article distributed under the terms described at http://journals.iucr.org/services/termsofuse.html.
spellingShingle Metal-Organic Papers
Robeyns, Koen
Alen, Jo
De Borggraeve, Wim M.
Compernolle, Frans
Van Meervelt, Luc
trans-Chlorido[6-chloro-4-(4-methoxy­benz­yl)-3-oxo-3,4-dihydro­pyrazin-2-yl]­bis­(triphenyl­phosphine)palladium(II)
title trans-Chlorido[6-chloro-4-(4-methoxy­benz­yl)-3-oxo-3,4-dihydro­pyrazin-2-yl]­bis­(triphenyl­phosphine)palladium(II)
title_full trans-Chlorido[6-chloro-4-(4-methoxy­benz­yl)-3-oxo-3,4-dihydro­pyrazin-2-yl]­bis­(triphenyl­phosphine)palladium(II)
title_fullStr trans-Chlorido[6-chloro-4-(4-methoxy­benz­yl)-3-oxo-3,4-dihydro­pyrazin-2-yl]­bis­(triphenyl­phosphine)palladium(II)
title_full_unstemmed trans-Chlorido[6-chloro-4-(4-methoxy­benz­yl)-3-oxo-3,4-dihydro­pyrazin-2-yl]­bis­(triphenyl­phosphine)palladium(II)
title_short trans-Chlorido[6-chloro-4-(4-methoxy­benz­yl)-3-oxo-3,4-dihydro­pyrazin-2-yl]­bis­(triphenyl­phosphine)palladium(II)
title_sort trans-chlorido[6-chloro-4-(4-methoxy­benz­yl)-3-oxo-3,4-dihydro­pyrazin-2-yl]­bis­(triphenyl­phosphine)palladium(ii)
topic Metal-Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2914967/
https://www.ncbi.nlm.nih.gov/pubmed/21200660
http://dx.doi.org/10.1107/S1600536807063441
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