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

被引：15

作者：

Vu, Thien Y. ^{[1
,2
]}

Chrostowska, Anna ^{[1
]}

Thi Kieu Xuan Huynh ^{[2
]}

Khayar, Said ^{[1
]}

Dargelos, Alain ^{[1
]}

Justyna, Katarzyna ^{[3
]}

Pasternak, Beata ^{[3
]}

Lesniak, Stanislaw ^{[3
]}

Wentrup, Curt ^{[4
]}

机构：

[1] Univ Pau & Pays Adour, CNRS, Inst Sci Analyt & Physicochim Environm & Mat, UMR 5254, F-64000 Pau, France

[2] Univ Natl Vietnam, Hanoi, Vietnam

[3] Univ Lodz, Dept Organ & Appl Chem, PL-91403 Lodz, Poland

[4] Univ Queensland, Sch Chem & Mol Biosci, Brisbane, Qld, Australia

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 44期

关键词：

density functional calculations; flash pyrolysis; heterocycles; photoelectron spectroscopy; radicals; ELECTRON-SPIN-RESONANCE; GAS-PHASE GENERATION; PHOTOELECTRON-SPECTROSCOPY; THERMAL TRANSFORMATIONS; CYCLIZATION; PYROLYSIS; POLYAZAPENTADIENES; AMIDES; ALKYL;

D O I：

10.1002/chem.201301663

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Thermal reactions of N-benzylidene- and N-(2-pyridylmethylidene)-tert-butylamines (5 and 13) under FVT conditions have been investigated. Unexpectedly, at 800 degrees C, compound 5 yields 1,2-dimethylindole and 3-methylisoquinoline. In the reaction of 13 at 800 degrees 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.

引用

页码：14983 / 14988

页数：6

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