在1,3 - 二羰基化合物存在下2,3 - 二甲基对苯二酚的电化学氧化

Electrochemical oxidation of 2,3-dimethylhydroquinone in the presence of 1,3-dicarbonyl compounds.

作者信息

Hosseiny Davarani Saied Saeed, Nematollahi Davood, Shamsipur Mojtaba, Najafi Nahid Mashkouri, Masoumi Leila, Ramyar Somayyeh

机构信息

Department of Chemistry, Shahid Beheshti University, Tehran, Iran.

出版信息

J Org Chem. 2006 Mar 3;71(5):2139-42. doi: 10.1021/jo0523767.

DOI:10.1021/jo0523767

PMID:16497004

Abstract

The electrooxidation of 2,3-dimethylhydroquinone (1) has been studied in the presence of 2-phenyl-1,3-indandione (3a), 3-hydroxy-1H-phenalen-1-one (3b), and 2-chloro-5,5-dimethyl-1,3-cyclohexanedione (3c) as CH acid nucleophiles in water/acetonitrile (85/15) solution, using cyclic voltammetry and controlled-potential coulometry. The results indicate that p-benzoquinone, generated by electrochemically driven oxidation of the 2,3-dimethylhydroquinone (1), is scavenged by 3a-c, to give related products (5a, 9b, 8c) via various electrochemical mechanisms. The electrochemical syntheses of 5a, 9b, and 8c have been successfully performed in one-pot in an undivided cell using an environmentally friendly method with high atomic economy.

摘要

在水/乙腈（85/15）溶液中，以2-苯基-1,3-茚二酮（3a）、3-羟基-1H-菲-1-酮（3b）和2-氯-5,5-二甲基-1,3-环己二酮（3c）作为碳氢酸性亲核试剂，采用循环伏安法和控制电位库仑法研究了2,3-二甲基对苯二酚（1）的电氧化反应。结果表明，由2,3-二甲基对苯二酚（1）的电化学驱动氧化生成的对苯醌被3a - c捕获，通过各种电化学机制生成相关产物（5a、9b、8c）。5a、9b和8c的电化学合成已在无隔膜电解池中一锅法成功完成，采用了具有高原子经济性的环境友好方法。