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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
Author(s) -
Vu Thien Y,
Chrostowska Anna,
Huynh Thi Kieu Xuan,
Khayar Saïd,
Dargelos Alain,
Justyna Katarzyna,
Pasternak Beata,
Leśniak Stanisław,
Wentrup Curt
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201301663
Subject(s) - thermal decomposition , chemistry , pyridine , decomposition , medicinal chemistry , x ray photoelectron spectroscopy , reaction mechanism , combinatorial chemistry , organic chemistry , catalysis , chemical engineering , engineering
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.