Base-induced rearrangement of tritylamines to imines: discovery and investigation of the mechanism
| dc.contributor.author | Theodorou, V. | en |
| dc.contributor.author | Skobridis, K. | en |
| dc.contributor.author | Karkatsoulis, A. | en |
| dc.date.accessioned | 2015-11-24T16:53:00Z | |
| dc.date.available | 2015-11-24T16:53:00Z | |
| dc.identifier.issn | 0040-4020 | - |
| dc.identifier.uri | https://olympias.lib.uoi.gr/jspui/handle/123456789/9956 | |
| dc.rights | Default Licence | - |
| dc.subject | tritylamide | en |
| dc.subject | tritylamine | en |
| dc.subject | imine | en |
| dc.subject | aryl or phenyl migration | en |
| dc.subject | hydride loss | en |
| dc.subject | base-induced rearrangement | en |
| dc.subject | bridged anionic intermediate | en |
| dc.subject | molecular rearrangement | en |
| dc.subject | carbanions | en |
| dc.subject | ketimines | en |
| dc.subject | intermediate | en |
| dc.subject | migration | en |
| dc.subject | catalysis | en |
| dc.subject | amines | en |
| dc.title | Base-induced rearrangement of tritylamines to imines: discovery and investigation of the mechanism | en |
| heal.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 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 |
| heal.access | campus | - |
| heal.fullTextAvailability | TRUE | - |
| heal.identifier.primary | DOI 10.1016/j.tet.2007.03.055 | - |
| heal.identifier.secondary | <Go to ISI>://000248133300009 | - |
| heal.identifier.secondary | http://ac.els-cdn.com/S0040402007004553/1-s2.0-S0040402007004553-main.pdf?_tid=dfa848c6-3a30-11e3-bdcd-00000aab0f6c&acdnat=1382346913_58ec829dbd2262fad7068abd973154e8 | - |
| heal.journalName | Tetrahedron | en |
| heal.journalType | peer reviewed | - |
| heal.language | en | - |
| heal.publicationDate | 2007 | - |
| heal.publisher | Elsevier | en |
| heal.recordProvider | Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας | el |
| heal.type | journalArticle | - |
| heal.type.el | Άρθρο Περιοδικού | el |
| heal.type.en | Journal article | en |
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