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

Davood Nematollahi Adel Ghorbani Amene Amani Hamid Salehzadeh Hadi Beiginejad

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

    通讯作者: Davood Nematollahi,
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-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.

English

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  • 发布日期:  2013-02-28
  • 收稿日期:  2012-09-11
  • 网络出版日期:  2013-01-15
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