Citation: Davood Nematollahi, Adel Ghorbani, Amene Amani, Hamid Salehzadeh, Hadi Beiginejad. Oxidative Diels-Alder reaction of 2, 5-dihydroxybenzoic acid with 1, 3-cyclopentadiene[J]. Chinese Chemical Letters, ;2013, 24(3): 205-207. shu

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

1.
Faculty of Chemistry, Bu-Ali Sina University, Hamedan 65178-38683, Iran

Corresponding author: Davood Nematollahi,
Received Date: 11 September 2012
Available Online: 15 January 2013

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.
- ECCEC pathway,
- Electrochemical oxidation,
- Diels-Alder reaction,
- 1, 3-Cyclopentadiene,
- 2, 5-Dihydroxybenzoic acid
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沈阳化工大学材料科学与工程学院沈阳 110142