New Reactions of N‐tert‐Butylimines; Formation of N‐Heterocycles by Methyl Radical Elimination on Flash Vacuum Thermolysis of N‐Benzylidene‐ and N‐(2‐Pyridylmethylidene)‐tert‐butylamines |
| |
| Authors: | Thien Y Vu Prof. Anna Chrostowska Prof. Thi Kieu Xuan Huynh Prof. Saïd Khayar Prof. Alain Dargelos Katarzyna Justyna Dr. Beata Pasternak Prof. Stanisław Leśniak Prof. Curt Wentrup |
| |
| Affiliation: | 1. Université de Pau et des Pays de l'Adour, Institut des Sciences Analytiques et de Physico‐Chimie pour l'Environnement et les Matériaux, UMR CNRS 5254, 64000 Pau (France);2. Université Nationale du Vietnam, à Ho Chi Minh Ville, 227 Nguen Van Cu, 5è arr Ho Chi Minh Ville (Vietnam);3. Department of Organic and Applied Chemistry, University of ?ód?, Tamka 12, 91‐403 ?ód? (Poland), Fax: (+48)?42‐635‐57‐44;4. School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane (Australia), Fax: (+61)?7‐3365‐4299 |
| |
| Abstract: | Thermal reactions of N‐benzylidene‐ and N‐(2‐pyridylmethylidene)‐tert‐butylamines ( 5 and 13 ) under FVT conditions have been investigated. Unexpectedly, at 800 °C, compound 5 yields 1,2‐dimethylindole and 3‐methylisoquinoline. In the reaction of 13 at 800 °C, 3‐methylimidazo[1,5‐a]pyridine was obtained as the major product. Mechanisms of these reactions have been proposed on the basis of DFT calculations. Furthermore, UV‐photoelectron spectroscopy combined with FVT has been applied for direct monitoring and characterization of the thermolysis products in situ. |
| |
| Keywords: | density functional calculations flash pyrolysis heterocycles photoelectron spectroscopy radicals |
|
|
