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Vu TY, Chrostowska A, Huynh TK, et al. 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. Chemistry. 2013;19(44):14983-8doi: 10.1002/chem.201301663.
Vu, T. Y., Chrostowska, A., Huynh, T. K., Khayar, S., Dargelos, A., Justyna, K., Pasternak, B., Leśniak, S., & Wentrup, C. (2013). 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. Chemistry (Weinheim an der Bergstrasse, Germany), 19(44), 14983-8. https://doi.org/10.1002/chem.201301663
Vu, Thien Y, et al. "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." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 19,44 (2013): 14983-8. doi: https://doi.org/10.1002/chem.201301663
Vu TY, Chrostowska A, Huynh TK, Khayar S, Dargelos A, Justyna K, Pasternak B, Leśniak S, Wentrup C. 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. Chemistry. 2013 Oct 25;19(44):14983-8. doi: 10.1002/chem.201301663. Epub 2013 Sep 20. PMID: 24108670.
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Chemistry. 2013 Oct 25;19(44):14983-8. doi: 10.1002/chem.201301663. Epub 2013 Sep 20.

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.

Chemistry (Weinheim an der Bergstrasse, Germany)

Thien Y Vu, Anna Chrostowska, Thi Kieu Xuan Huynh, Saïd Khayar, Alain Dargelos, Katarzyna Justyna, Beata Pasternak, Stanisław Leśniak, Curt Wentrup

Affiliations

  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); Université Nationale du Vietnam, à Ho Chi Minh Ville, 227 Nguen Van Cu, 5è arr Ho Chi Minh Ville (Vietnam).

PMID: 24108670 DOI: 10.1002/chem.201301663

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.

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

Keywords: density functional calculations; flash pyrolysis; heterocycles; photoelectron spectroscopy; radicals

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