Department of Chemistry, University of California, Davis, Davis, CA 95616, USA.
Department of Biochemistry & Molecular Medicine, School of Medicine, University of California, Davis, Sacramento, CA 95817, USA.
Org Biomol Chem. 2021 Sep 15;19(35):7575-7580. doi: 10.1039/d1ob01450a.
Azobenzenes are widely used as dyes and photochromic compounds, with the Baeyer-Mills reaction serving as the most common method for their preparation. This transformation is often plagued by low yields due to the formation of undesired azoxybenzene. Here, we explore electronic effects dictating the formation of the azoxybenzene side-product. Using calculated oxidation potentials, we were able to predict reaction outcomes and improve reaction efficiency simply by modulating the oxidation potential of the arylamine component.
偶氮苯被广泛用作染料和光致变色化合物，拜耳-米尔斯反应是其最常用的制备方法。由于副产物偶氮苯的形成，该转化往往产率较低。在这里，我们探讨了决定偶氮苯副产物形成的电子效应。使用计算得到的氧化电势，我们能够通过调节芳基胺组分的氧化电势来预测反应结果并提高反应效率。
