The oxidation of the alpha-carbon of amines in hydrothermal condition: an alternative synthetic route of compounds containing amide bond

被引：2

作者：

Bai, Xueyin ^{[1
]}

Liu, Ziwei ^{[1
]}

Ye, Kaiqi ^{[2
]}

Wang, Yu ^{[1
]}

Zhang, Xianlong ^{[1
]}

Yue, Huijuan ^{[1
]}

Tian, Ge ^{[1
]}

Feng, Shouhua ^{[1
]}

机构：

[1] Jilin Univ, Coll Chem, State Key Lab Inorgan Synth & Preparat Chem, Changchun 130012, Peoples R China

[2] Jilin Univ, State Key Lab Supramol Struct & Mat, Changchun 130012, Peoples R China

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 02期

基金：

中国国家自然科学基金;

关键词：

Tertiary amines; Oxidation; Amides; Hydrothermal condition; Radical reaction; CHEMICAL EVOLUTION; ORGANIC-COMPOUNDS; ACIDS; DIOXIDE; ORIGIN; TRIETHYLAMINE; PEPTIDES; SYSTEMS; LIFE;

D O I：

10.1016/j.tetlet.2013.11.005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Here we report experimental evidence for the simple synthesis of N,N-diethylhydroxylamine and an amide bond formation reaction from oxidation of the alpha-carbon of tertiary amines by the reaction of triethylamine and hydrogen peroxide in hydrothermal conditions. It is proved that 120 degrees C is a turning point: when the temperature is lower than that, the main product is N,N-diethylhydroxylamine as a result of a cope rearrangement reaction mechanism; on the contrary, the product is more complex and the main products are amides via a radical chain mechanism involving three steps: initiation, propagation, and oxidation, followed by decarbonylation and electrocyclization because the radical is easier to form under high temperature. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：319 / 321

页数：3

共 14 条

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