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
Résumé
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. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.