کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5230442 | 1383695 | 2007 | 6 صفحه PDF | دانلود رایگان |
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.
A cationotropic intramolecular aryl rearrangement, via an anionic intermediate, of tritylamines to imines upon treatment with n-butyl lithium is suggested. The anionic intermediate is better stabilized by electron-withdrawing substituents.
Journal: Tetrahedron - Volume 63, Issue 20, 14 May 2007, Pages 4284-4289