Oxidative Diels-Alder reaction of 2,5-dihydroxybenzoic acid with 1,3-cyclopentadiene  

作　　者：Davood Nematollahi Adel Ghorbani Amene Amani Hamid Salehzadeh Hadi Beiginejad 

机构地区：[1]Faculty of Chemistry,Bu-Ali Sina University

出　　处：《Chinese Chemical Letters》2013年第3期205-207,共3页中国化学快报（英文版）

基　　金：the Bu-Ali Sina University Research Council and Center of Excellence in Development of Environmentally Friendly Methods for Chemical Synthesis(CEDEFMCS) for their support of this work

摘　　要：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-l,4-dienecarboxylic acid （lox）, decarboxylation reaction, electrooxidation and Diels-Alder reaction. The electrochemical synthesis of 5 was performed in a one- pot reaction, without toxic reagents, at a carbon electrode in a simple cell using an environmentally friendlv method.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-l,4-dienecarboxylic acid （lox）, decarboxylation reaction, electrooxidation and Diels-Alder reaction. The electrochemical synthesis of 5 was performed in a one- pot reaction, without toxic reagents, at a carbon electrode in a simple cell using an environmentally friendlv method.

关 键 词：ECCEC pathwayElectrochemical oxidationDiels-Alder reaction1 3-Cyclopentadiene2 5-Dihydroxybenzoic acid 

分 类 号：O621.25[理学—有机化学]