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

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

Theodorou, V. (EN)

Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας (EL)
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. (EN)

tritylamide (EN)


Tetrahedron (EN)

English

2007


Elsevier (EN)



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