Factors affecting the competitive reduction of 8,8-dimethylnaphthalene-1,4, 5(8H)-trione in a Diels-Alder cycloaddition with hydroxysulfinyldienes

Iriux Almodovar, Wilson Cardona, Tomás Delgado-Castro, Gerald Zapata-Torres, Marcos Caroli Rezende, Ramiro Araya-Maturana

Resultado de la investigación: Article

Resumen

Competing reduction and cycloaddition products were formed in the reaction of 8,8-dimethylnaphthalene-1,4,5(8H)-trione with a hydroxysulfinyldiene. The ratio of reduction to cycloaddition products depended on the stereochemistry of the diene and on the solvent employed, being higher in ethanol than in benzene. The ratio was also affected by the addition of Lewis acids, decreasing in the order BF3 = Al2O3 > MgCl2 > ZnCl2. The results help to explain and predict the occurrence of these competing processes in Diels-Alder cycloadditions involving quinonedienophiles.

Idioma originalEnglish
Páginas (desde-hasta)1021-1026
Número de páginas6
PublicaciónJournal of the Iranian Chemical Society
Volumen11
N.º4
DOI
EstadoPublished - 2014

Huella dactilar

Cycloaddition
Lewis Acids
Stereochemistry
Magnesium Chloride
Benzene
Ethanol
1,4-dimethylnaphthalene

ASJC Scopus subject areas

  • Chemistry(all)

Citar esto

Almodovar, Iriux ; Cardona, Wilson ; Delgado-Castro, Tomás ; Zapata-Torres, Gerald ; Rezende, Marcos Caroli ; Araya-Maturana, Ramiro. / Factors affecting the competitive reduction of 8,8-dimethylnaphthalene-1,4, 5(8H)-trione in a Diels-Alder cycloaddition with hydroxysulfinyldienes. En: Journal of the Iranian Chemical Society. 2014 ; Vol. 11, N.º 4. pp. 1021-1026.
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abstract = "Competing reduction and cycloaddition products were formed in the reaction of 8,8-dimethylnaphthalene-1,4,5(8H)-trione with a hydroxysulfinyldiene. The ratio of reduction to cycloaddition products depended on the stereochemistry of the diene and on the solvent employed, being higher in ethanol than in benzene. The ratio was also affected by the addition of Lewis acids, decreasing in the order BF3 = Al2O3 > MgCl2 > ZnCl2. The results help to explain and predict the occurrence of these competing processes in Diels-Alder cycloadditions involving quinonedienophiles.",
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Factors affecting the competitive reduction of 8,8-dimethylnaphthalene-1,4, 5(8H)-trione in a Diels-Alder cycloaddition with hydroxysulfinyldienes. / Almodovar, Iriux; Cardona, Wilson; Delgado-Castro, Tomás; Zapata-Torres, Gerald; Rezende, Marcos Caroli; Araya-Maturana, Ramiro.

En: Journal of the Iranian Chemical Society, Vol. 11, N.º 4, 2014, p. 1021-1026.

Resultado de la investigación: Article

TY - JOUR

T1 - Factors affecting the competitive reduction of 8,8-dimethylnaphthalene-1,4, 5(8H)-trione in a Diels-Alder cycloaddition with hydroxysulfinyldienes

AU - Almodovar, Iriux

AU - Cardona, Wilson

AU - Delgado-Castro, Tomás

AU - Zapata-Torres, Gerald

AU - Rezende, Marcos Caroli

AU - Araya-Maturana, Ramiro

PY - 2014

Y1 - 2014

N2 - Competing reduction and cycloaddition products were formed in the reaction of 8,8-dimethylnaphthalene-1,4,5(8H)-trione with a hydroxysulfinyldiene. The ratio of reduction to cycloaddition products depended on the stereochemistry of the diene and on the solvent employed, being higher in ethanol than in benzene. The ratio was also affected by the addition of Lewis acids, decreasing in the order BF3 = Al2O3 > MgCl2 > ZnCl2. The results help to explain and predict the occurrence of these competing processes in Diels-Alder cycloadditions involving quinonedienophiles.

AB - Competing reduction and cycloaddition products were formed in the reaction of 8,8-dimethylnaphthalene-1,4,5(8H)-trione with a hydroxysulfinyldiene. The ratio of reduction to cycloaddition products depended on the stereochemistry of the diene and on the solvent employed, being higher in ethanol than in benzene. The ratio was also affected by the addition of Lewis acids, decreasing in the order BF3 = Al2O3 > MgCl2 > ZnCl2. The results help to explain and predict the occurrence of these competing processes in Diels-Alder cycloadditions involving quinonedienophiles.

KW - Cycloaddition

KW - Diels-Alder

KW - Quinone

KW - Reduction

KW - Sulfinyldienes

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U2 - 10.1007/s13738-013-0370-x

DO - 10.1007/s13738-013-0370-x

M3 - Article

AN - SCOPUS:84904705868

VL - 11

SP - 1021

EP - 1026

JO - Journal of the Iranian Chemical Society

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