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2-azaallylic rearrangement in homogeneous systems |
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| Authors: | Rogman Agnieszka Gancarz Roman Domagalska Beata W Wilk Kazimiera A |
| Affiliation: | (1) Institute of Organic Chemistry, Biochemistry and Biotechnology, Wrocław University of Technology, Wyb. Wyspiańskiego 27, 50-370 Wrocław, Poland;(2) Instittute of Organic and Polymer Technology, Wrocław University of Technology, Wyb. Wyspiańskiego 27, 50-370 Wrocław, Poland |
| Abstract: | In this work we present mechanism of the base-catalyzed 2-azaallylic rearrangement in homogeneous media. Detailed 2-azaallylic rearrangement studies have shown that tautomerism of derivatives of benzylidenebenzhydrylamines and N-fluorenylidenebenzylamines is not adequately encomposed by the Hammet equation and the equilibrium constant in the case of studied derivatives depends on the electronic as well as steric factors of the azaallylic system substituents. The presence of steric interactions which influence the equilibrium state has been additionally confirmed by means of crystallographic and molecular mechanics data as well as NOE studies. This revised version was published online in August 2006 with corrections to the Cover Date. |
| Keywords: | base-catalyzed 2-azaallylic rearrangement fluorenylidene imines benzhydrylidene imines |
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