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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 |
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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 |
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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. |
format | Text |
id | pubmed-2914967 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2007 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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