Department of Chemistry, Ben-Gurion University of the Negev, Beer Sheva 84105, Israel.
Org Biomol Chem. 2012 May 21;10(19):3906-12. doi: 10.1039/c2ob06878h. Epub 2012 Apr 4.
Anodic oxidation of N-aryl-2,2-diphenylacetamides in acetonitrile undergoes three types of bond-cleavage, one between the benzylic carbon and the carbonyl group, the second between a carbonyl and 'N', and the third between the 'N' atom and aryl group. The selectivity of the cleavage and nature of emerged products is highly dependent on the nature of substituent attached to the aryl group. For example, electron-withdrawing groups direct the benzyl-carbonyl bond-breaking whereas electron-donating substituents favor the N-aryl bond cleavage. The type of products obtained involve benzophenone, 2,2-diphenylacetamide, N-(diphenylmethylene)acetamide, N-(diphenylmethyl)acetamide, α-lactam (1-acetyl-3,3-diphenylaziridin-2-one, as a 1 : 1 complex with 2,4-dinitroaniline) and aniline derivatives.
N-芳基-2,2-二苯基乙酰胺在乙腈中的阳极氧化经历三种类型的键断裂，一种是苄基碳和羰基之间，另一种是羰基和 'N' 之间，第三种是 'N' 原子和芳基之间。断裂的选择性和出现的产物的性质高度取决于连接在芳基上的取代基的性质。例如，吸电子基团促使苄基-羰基键断裂，而供电子取代基有利于 N-芳基键断裂。得到的产物类型包括二苯甲酮、2,2-二苯基乙酰胺、N-(二苯基亚甲基)乙酰胺、N-(二苯甲基)乙酰胺、α-内酰胺（1-乙酰基-3,3-二苯基氮杂环丁-2-酮，与 2,4-二硝基苯胺以 1:1 配合物形式存在）和苯胺衍生物。
