Department of Organic Chemistry, University of Alcalá , 28871 Alcalá de Henares, Madrid, Spain.
J Org Chem. 2013 Sep 20;78(18):9477-81. doi: 10.1021/jo401264w. Epub 2013 Sep 4.
The one-pot concomitant electrochemical reduction of phenanthrenequinones (1, 2) and arenediazonium salts (3a-f) led to the formation of 1,3,4-oxadiazol-2(3H)-ones (4a-f, 5a) and dibenzo[c,e]azepines (6a-f) when N-methylformamide was used as the solvent. A new pathway, different from those previously described with other aprotic solvents, is proposed. The experimental data support a radical mechanism for the electrochemical process followed by an internal rearrangement to give the products.
一锅法同时电化学还原菲醌（1，2）和芳基重氮盐（3a-f），当使用 N-甲基甲酰胺作为溶剂时，生成 1,3,4-噁二唑-2(3H)-酮（4a-f，5a）和二苯并[c,e]氮杂䓬（6a-f）。提出了一种与以前使用其他非质子溶剂描述的不同的新途径。实验数据支持电化学过程遵循自由基机制，然后进行内部重排得到产物。
