127787-74-0Relevant articles and documents
Base-induced rearrangement of tritylamines to imines: discovery and investigation of the mechanism
Theodorou, Vassiliki,Skobridis, Konstantinos,Karkatsoulis, Aris
, p. 4284 - 4289 (2007/10/03)
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.
