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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 |
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| Authors: | Iriux Almodovar Wilson Cardona Tomás Delgado-Castro Gerald Zapata-Torres Marcos Caroli Rezende Ramiro Araya-Maturana |
| Institution: | 1. Departamento de Ciencias del Ambiente, Facultad de Química y Biología, Universidad de Santiago de Chile, Avenida B. O’Higgins 3363, Estación Central, CP 9160000, Santiago, Chile 2. Departamento de Ciencias Químicas, Universidad Andrés Bello, Autopista Concepción-Talcahuano 7100, Concepción, Chile 3. Departamento de Ciencias Químicas, Universidad Andrés Bello, República 237, Santiago, Chile 4. Departamento de Química Inorgánica y Analítica, Universidad de Chile, Casilla 233, Santiago 1, Chile 5. Departamento de Química Orgánica y Físico-Química, Universidad de Chile, Casilla 233, Santiago 1, Chile |
| 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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