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

V Theodorou, K Skobridis, A Karkatsoulis

Index: Theodorou, Vassiliki; Skobridis, Konstantinos; Karkatsoulis, Aris Tetrahedron, 2007 , vol. 63, # 20 p. 4284 - 4289

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Citation Number: 7

Abstract

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 ...