Meso and racemic 1,1-bis (benzylsulfinyl)-2-ethylbutane. A b-disulfoxide pro-ligand with steric restrictions

O. M. Zárraga, N. Y. Moreno, O. C. Franco

Resultado de la investigación: Article

1 Cita (Scopus)

Resumen

Coordination chemistry of disulfoxides is of interest in inorganic chemistry given the well-known metal coordination through oxygen or sulfur atoms.1 Ethylene and propylene bridged disulfoxide pro-ligands, coordinate to metals, forming coordinated and chelated complexes, demonstrating its flexibility in the formation of such complexes.2 Some of these compounds have demonstrated interesting properties in medicinal chemistry3 and asymmetric catalysis4 and their synthesis is of importance for bioorganic studies. The presence of two stereogenic centers allows the existence of the meso and racemic forms in disulfoxides. Previous studies on b-disulfoxides5 in our laboratories have led to the synthesis and spectroscopic study (1H-NMR, FT-IR) of both diastereomeric forms. In this work we report the synthesis and structural analysis of meso-(2)- and racemic-(3)-1,1-bis(benzylsulfinyl)-2-ethylbutane (Scheme1), with high steric requirement around both sulfinyl groups when a branched aliphatic carbon chain is introduced in the a-carbon. An increase in selectivity for small radius metal ions was achieved by compression of the pro-ligand coordination radius. These kind of compounds have not been previously studied.

Idioma originalEnglish
Páginas (desde-hasta)3157-3159
Número de páginas3
PublicaciónJournal of the Chilean Chemical Society
Volumen61
N.º4
EstadoPublished - 2016
Publicado de forma externa

Huella dactilar

Ligands
Carbon
Metal forming
Sulfur
Structural analysis
Metal ions
Metals
Nuclear magnetic resonance
Oxygen
ethylene
Inorganic Chemistry
propylene

ASJC Scopus subject areas

  • Chemistry(all)

Citar esto

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title = "Meso and racemic 1,1-bis (benzylsulfinyl)-2-ethylbutane. A b-disulfoxide pro-ligand with steric restrictions",
abstract = "Coordination chemistry of disulfoxides is of interest in inorganic chemistry given the well-known metal coordination through oxygen or sulfur atoms.1 Ethylene and propylene bridged disulfoxide pro-ligands, coordinate to metals, forming coordinated and chelated complexes, demonstrating its flexibility in the formation of such complexes.2 Some of these compounds have demonstrated interesting properties in medicinal chemistry3 and asymmetric catalysis4 and their synthesis is of importance for bioorganic studies. The presence of two stereogenic centers allows the existence of the meso and racemic forms in disulfoxides. Previous studies on b-disulfoxides5 in our laboratories have led to the synthesis and spectroscopic study (1H-NMR, FT-IR) of both diastereomeric forms. In this work we report the synthesis and structural analysis of meso-(2)- and racemic-(3)-1,1-bis(benzylsulfinyl)-2-ethylbutane (Scheme1), with high steric requirement around both sulfinyl groups when a branched aliphatic carbon chain is introduced in the a-carbon. An increase in selectivity for small radius metal ions was achieved by compression of the pro-ligand coordination radius. These kind of compounds have not been previously studied.",
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Meso and racemic 1,1-bis (benzylsulfinyl)-2-ethylbutane. A b-disulfoxide pro-ligand with steric restrictions. / Zárraga, O. M.; Moreno, N. Y.; Franco, O. C.

En: Journal of the Chilean Chemical Society, Vol. 61, N.º 4, 2016, p. 3157-3159.

Resultado de la investigación: Article

TY - JOUR

T1 - Meso and racemic 1,1-bis (benzylsulfinyl)-2-ethylbutane. A b-disulfoxide pro-ligand with steric restrictions

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AU - Moreno, N. Y.

AU - Franco, O. C.

PY - 2016

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N2 - Coordination chemistry of disulfoxides is of interest in inorganic chemistry given the well-known metal coordination through oxygen or sulfur atoms.1 Ethylene and propylene bridged disulfoxide pro-ligands, coordinate to metals, forming coordinated and chelated complexes, demonstrating its flexibility in the formation of such complexes.2 Some of these compounds have demonstrated interesting properties in medicinal chemistry3 and asymmetric catalysis4 and their synthesis is of importance for bioorganic studies. The presence of two stereogenic centers allows the existence of the meso and racemic forms in disulfoxides. Previous studies on b-disulfoxides5 in our laboratories have led to the synthesis and spectroscopic study (1H-NMR, FT-IR) of both diastereomeric forms. In this work we report the synthesis and structural analysis of meso-(2)- and racemic-(3)-1,1-bis(benzylsulfinyl)-2-ethylbutane (Scheme1), with high steric requirement around both sulfinyl groups when a branched aliphatic carbon chain is introduced in the a-carbon. An increase in selectivity for small radius metal ions was achieved by compression of the pro-ligand coordination radius. These kind of compounds have not been previously studied.

AB - Coordination chemistry of disulfoxides is of interest in inorganic chemistry given the well-known metal coordination through oxygen or sulfur atoms.1 Ethylene and propylene bridged disulfoxide pro-ligands, coordinate to metals, forming coordinated and chelated complexes, demonstrating its flexibility in the formation of such complexes.2 Some of these compounds have demonstrated interesting properties in medicinal chemistry3 and asymmetric catalysis4 and their synthesis is of importance for bioorganic studies. The presence of two stereogenic centers allows the existence of the meso and racemic forms in disulfoxides. Previous studies on b-disulfoxides5 in our laboratories have led to the synthesis and spectroscopic study (1H-NMR, FT-IR) of both diastereomeric forms. In this work we report the synthesis and structural analysis of meso-(2)- and racemic-(3)-1,1-bis(benzylsulfinyl)-2-ethylbutane (Scheme1), with high steric requirement around both sulfinyl groups when a branched aliphatic carbon chain is introduced in the a-carbon. An increase in selectivity for small radius metal ions was achieved by compression of the pro-ligand coordination radius. These kind of compounds have not been previously studied.

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