Oxidative Diels-Alder reaction of 2, 5-dihydroxybenzoic acid with 1, 3-cyclopentadiene |
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Authors: | Davood Nematollahi Adel Ghorbani Amene Amani Hamid Salehzadeh Hadi Beiginejad |
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Institution: | Faculty of Chemistry, Bu-Ali Sina University, Hamedan 65178-38683, Iran |
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Abstract: | The electrochemical oxidation of 2,5-dihydroxybenzoic acid (1) has been studied in the presence of 1,3-cyclopentadiene (2) as a diene in water/ethanol (40/60, v/v) mixture using cyclic voltammetry and controlled-potential coulometry. A plausible mechanism for the oxidation of 1 in the presence of 2 is presented. Compound 1 was converted into bis-adduct 5 via electrooxidation, Diels-Alder reaction of 2 to anodically generated 3,6-dioxocyclohexa-1,4-dienecarboxylic acid (1ox), decarboxylation reaction, electrooxidation and Diels-Alder reaction. The electrochemical synthesis of 5 was performed in a onepot reaction, without toxic reagents, at a carbon electrode in a simple cell using an environmentally friendly method. |
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Keywords: | ECCEC pathway Electrochemical oxidation Diels-Alder reaction 1 3-Cyclopentadiene 2 5-Dihydroxybenzoic acid |
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