Base-induced rearrangement of tritylamines to imines: discovery and investigation of the mechanism |
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Authors: | Vassiliki Theodorou Konstantinos Skobridis Aris Karkatsoulis |
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Institution: | Department of Chemistry, Section of Organic Chemistry and Biochemistry, University of Ioannina, GR-451 10 Ioannina, Greece |
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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. |
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Keywords: | Tritylamide Tritylamine Imine Aryl or phenyl migration Hydride loss Base-induced rearrangement Bridged anionic intermediate |
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