Base-induced rearrangement of tritylamines to imines: discovery and investigation of the mechanism
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Authors
Theodorou, V.
Skobridis, K.
Karkatsoulis, A.
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Elsevier
Abstract
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peer reviewed
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Tetrahedron
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Description
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.
Description
Keywords
tritylamide, tritylamine, imine, aryl or phenyl migration, hydride loss, base-induced rearrangement, bridged anionic intermediate, molecular rearrangement, carbanions, ketimines, intermediate, migration, catalysis, amines
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<Go to ISI>://000248133300009
http://ac.els-cdn.com/S0040402007004553/1-s2.0-S0040402007004553-main.pdf?_tid=dfa848c6-3a30-11e3-bdcd-00000aab0f6c&acdnat=1382346913_58ec829dbd2262fad7068abd973154e8
http://ac.els-cdn.com/S0040402007004553/1-s2.0-S0040402007004553-main.pdf?_tid=dfa848c6-3a30-11e3-bdcd-00000aab0f6c&acdnat=1382346913_58ec829dbd2262fad7068abd973154e8
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en
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Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας