THE ELECTROCHEMICAL DEGRADATION OF QUATERNARY AMMONIUM SALTS .2. THE MECHANISM OF THE COUPLING REACTION
THE ELECTROCHEMICAL DEGRADATION OF QUATERNARY AMMONIUM SALTS .2. THE MECHANISM OF THE COUPLING REACTION
复制标题
DOI：
10.1021/ja01492a017
复制
发表时间：
1960-01-01
影响因子：
15
通讯作者：
PETERSEN, RC
中科院分区：
文献类型：
--
作者：
ROSS, SD;FINKELSTEIN, M;PETERSEN, RC
含苄基、芴基、肉桂基、对甲氧基苄基或苯乙基的硝酸季铵盐在N，N-二甲基乙酰胺或二甲基甲酰胺中阴极分解，得到这些自由基的偶联产物。该反应涉及自由基的产生和二聚化，在阴极处的单电子转移中形成。本实验室以前的一份报告1表明，电解某些季铵盐的水溶液，会使连接在氮上的一个烷基裂解，生成烃和叔胺。对于一种盐，苄基二甲基苯胺三氟乙酸盐，在水和二甲基乙酰胺中进行电解。在水中，产物是甲苯和二甲基苯胺，但在后者溶剂中，得到相同的胺和联苄。我们现在的目的是
The cathodic decomposition inN, N-dimethylacetamide or dimethylformamide of quaternary ammonium nitrates con-taining benzyl, fluorenyl, cinnamyl, J>-methoxybenzyl or-phenylethyl groups yields the coupling products of these radicals. The reaction involves the generation and dimerization of free radicals, formed in a one-electron transfer at the cathode. This is indicated by the fact that¿-a-phenylethyltrimethylammonium nitrate gives only inactive products.In a previous report from this Laboratory, 1 it was shown thatthe electrolysis of aqueous solutions of selected quaternary ammonium salts resulted in the cleavage of one of the alkyl groups attached to nitrogen to form a hydrocarbon and a tertiary amine. For one salt, benzyldimethylanilinium trifluoroacetate, the electrolyses were carried out in both water and dimethylacetamide. In water the products were toluene and dimethylaniline but, in the latter solvent, the same amine and bibenzyl were obtained. It is our present purpose to show