Base-induced rearrangement of tritylamines to imines: discovery and investigation of the mechanism
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Theodorou, V.
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Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας
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Theodorou, V.
(EN)
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. (C) 2007 Elsevier Ltd. All rights reserved.
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