Base-induced rearrangement of tritylamines to imines: discovery and investigation of the mechanism

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• 作者：Vassiliki Theodorou ; Konstantinos Skobridis ; Aris Karkatsoulis
• 关键词：Tritylamide ; Tritylamine ; Imine ; Aryl or phenyl migration ; Hydride loss ; Base-induced rearrangement ; Bridged anionic intermediate
• 刊名：Tetrahedron
• 出版年：2007
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：14 May 2007
• 卷：63
• 期：20
• 页码：4284-4289
• 文件大小：217 K

摘要

An unexpected compound, the aniline derived benzophenone imine, was isolated when tritylamine was treated with n-BuLi and alkyl halides, during the formation of N-alkyl tritylamines, in the process of preparing primary amines. A nucleophilic attack of the nitrogen anion of tritylamide on the adjacent C-bonded phenyl, either substituted or not, involving a bridging anionic intermediate, is proposed for this base-induced tritylamine rearrangement to produce the corresponding imine. Electron-withdrawing groups in the aromatic ring, favoring the negative charge development, affect the relative migratory tendencies.