New reactions of N-tert-butylimines; formation of N-heterocycles by methyl radical elimination on flash vacuum thermolysis of N-benzylidene- and N-(2-pyridyl-methylidene)-tert-butylamines

Vu, Thien Y, Chrostowska, Anna, Huynh, Thi Kieu Xuan, Khayar, Saïd, Dargelos, Alain, Justyna, Katarzyna, Pasternak, Beata, Leśniak, Stanisław and Wentrup, Curt (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-pyridyl-methylidene)-tert-butylamines. Chemistry: A European Journal, 19 44: 14983-14988. doi:10.1002/chem.201301663

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Author Vu, Thien Y
Chrostowska, Anna
Huynh, Thi Kieu Xuan
Khayar, Saïd
Dargelos, Alain
Justyna, Katarzyna
Pasternak, Beata
Leśniak, Stanisław
Wentrup, Curt
Title New reactions of N-tert-butylimines; formation of N-heterocycles by methyl radical elimination on flash vacuum thermolysis of N-benzylidene- and N-(2-pyridyl-methylidene)-tert-butylamines
Formatted title
New reactions of N-tert-butylimines; formation of N-heterocycles by methyl radical elimination on flash vacuum thermolysis of N-benzylidene- and N-(2-pyridyl-methylidene)-tert-butylamines
Journal name Chemistry: A European Journal   Check publisher's open access policy
ISSN 0947-6539
1521-3765
Publication date 2013-10-25
Year available 2013
Sub-type Article (original research)
DOI 10.1002/chem.201301663
Open Access Status
Volume 19
Issue 44
Start page 14983
End page 14988
Total pages 6
Place of publication Weinheim, Germany
Publisher Wiley - V C H Verlag
Language eng
Formatted 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-ɑ]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.
Keyword Density functional calculations
Flash pyrolysis
Heterocycles
Photoelectron spectroscopy
Radicals
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ
Additional Notes Article first published online: 20 SEP 2013

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2014 Collection
School of Chemistry and Molecular Biosciences
 
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Citation counts: TR Web of Science Citation Count  Cited 11 times in Thomson Reuters Web of Science Article | Citations
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Created: Mon, 30 Sep 2013, 23:24:16 EST by Mrs Louise Nimwegen on behalf of School of Chemistry & Molecular Biosciences