Electrochemical synthesis of 3,5-disubstituted isoxazoles

被引：20

作者：

Xiao, Huan-Lan ^{[1
]}

Zeng, Cheng-Chu ^{[1
]}

Tian, Hong-Yu ^{[2
]}

Hu, Li-Ming ^{[1
]}

Little, R. Daniel ^{[3
]}

机构：

[1] Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China

[2] Beijing Technol & Business Univ, Food Coll, Beijing 100147, Peoples R China

[3] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

来源：

JOURNAL OF ELECTROANALYTICAL CHEMISTRY | 2014年 / 727卷

基金：

美国国家科学基金会; 北京市自然科学基金; 中国国家自然科学基金;

关键词：

Electrochemical synthesis; Isoxazoles; Chalcone oximes; NITRILE OXIDES; REGIOSELECTIVE SYNTHESIS; CONVENIENT METHOD; CYCLOADDITION; EFFICIENT; OXIMES; ELECTROSYNTHESIS; GENERATION; OXIDATION; ALKENES;

D O I：

10.1016/j.jelechem.2014.06.008

中图分类号：

O65 [分析化学];

学科分类号：

070302 ; 081704 ;

摘要：

The electrochemical oxidation of chalcone oximes has been explored using preparative scale electrolysis and cyclic voltammetry (CV). The results show that a constant current electrolysis of chalcone oximes in an undivided cell affords the corresponding isoxazoles in moderate to good yields, using graphite as the working electrode and NaClO4/CH3OH as the supporting electrolyte. The cyclic voltammograms for nearly all of the chalcone oximes investigated exhibit only one oxidation peak. On the basis of preparative electrolysis results and CV analysis, a reaction mechanism, involving a combination of electrochemically-generated base and an iminoxy radical intermediate, is proposed. (C) 2014 Elsevier B.V. All rights reserved.

引用

页码：120 / 124

页数：5

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