Unusual reactivity of N-tert-butylimines under FVT conditions
Thermal reactions of N-tert-butyl-(E)-crotonaldimine (1a) and 1,4-di-(tert-butyl)-1,4-diazabuta-1,3-dien (glyoxal-bis-N-tert-butylimine) (1b) under FVT conditions have been studied. It has been found that at 800 °C compound 1a yielded pyrrole and crotononitrile, presumably via homolytic t-Bu–N bond...
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Published in | Tetrahedron Vol. 69; no. 2; pp. 722 - 729 |
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Main Authors | , , , , , , , |
Format | Journal Article |
Language | English |
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Abstract | Thermal reactions of N-tert-butyl-(E)-crotonaldimine (1a) and 1,4-di-(tert-butyl)-1,4-diazabuta-1,3-dien (glyoxal-bis-N-tert-butylimine) (1b) under FVT conditions have been studied. It has been found that at 800 °C compound 1a yielded pyrrole and crotononitrile, presumably via homolytic t-Bu–N bond cleavage and formation of the iminyl radical. In the reaction of 1b at 800 °C, 2-methylimidazole (4b) has been obtained unexpectedly as the major product. The mechanism of these reactions has been proposed. Furthermore, combined FVT and UV-photoelectron spectroscopy have been applied for direct generation and in situ characterization of compounds 1a and 1b under thermal activation conditions.
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AbstractList | Thermal reactions of N-tert-butyl-(E)-crotonaldimine (1a) and 1,4-di-(tert-butyl)-1,4-diazabuta-1,3-dien (glyoxal-bis-N-tert-butylimine) (1b) under FVT conditions have been studied. It has been found that at 800 degrees C compound la yielded pyrrole and crotononitrile, presumably via homolytic t-Bu-N bond cleavage and formation of the iminyl radical. In the reaction of 1b at 800 degrees C, 2-methylimidazole (4b) has been obtained unexpectedly as the major product. The mechanism of these reactions has been proposed. Furthermore, combined FVT and UV-photoelectron spectroscopy have been applied for direct generation and in situ characterization of compounds 1a and 1b under thermal activation conditions. (c) 2012 Elsevier Ltd. All rights reserved. Thermal reactions of N-tert-butyl-(E)-crotonaldimine (1a) and 1,4-di-(tert-butyl)-1,4-diazabuta-1,3-dien (glyoxal-bis-N-tert-butylimine) (1b) under FVT conditions have been studied. It has been found that at 800 °C compound 1a yielded pyrrole and crotononitrile, presumably via homolytic t-Bu–N bond cleavage and formation of the iminyl radical. In the reaction of 1b at 800 °C, 2-methylimidazole (4b) has been obtained unexpectedly as the major product. The mechanism of these reactions has been proposed. Furthermore, combined FVT and UV-photoelectron spectroscopy have been applied for direct generation and in situ characterization of compounds 1a and 1b under thermal activation conditions. [Display omitted] Thermal reactions of N-tert-butyl-(E)-crotonaldimine (1a) and 1,4-di-(tert-butyl)-1,4-diazabuta-1,3-dien (glyoxal-bis-N-tert-butylimine) (1b) under FVT conditions have been studied. It has been found that at 800 °C compound 1a yielded pyrrole and crotononitrile, presumably via homolytic t-BueN bond cleavage and formation of the iminyl radical. In the reaction of 1b at 800 °C, 2-methylimidazole (4b) has been obtained unexpectedly as the major product. The mechanism of these reactions has been proposed. Furthermore, combined FVT and UV-photoelectron spectroscopy have been applied for direct generation and in situ characterization of compounds 1a and 1b under thermal activation conditions. © 2012 Elsevier Ltd. All rights reserved. Thermal reactions of N-tert-butyl-(E)-crotonaldimine (1a) and 1,4-di-(tert-butyl)-1,4-diazabuta-1,3-dien (glyoxal-bis-N-tert-butylimine) (1b) under FVT conditions have been studied. It has been found that at 800ANB degree C compound 1a yielded pyrrole and crotononitrile, presumably via homolytic t-BuaN bond cleavage and formation of the iminyl radical. In the reaction of 1b at 800ANB degree C, 2-methylimidazole (4b) has been obtained unexpectedly as the major product. The mechanism of these reactions has been proposed. Furthermore, combined FVT and UV-photoelectron spectroscopy have been applied for direct generation and in situ characterization of compounds 1a and 1b under thermal activation conditions. |
Author | Vu, Thien Y. Leśniak, Stanisław Khayar, Saïd Xuan Huynh, Thi Kieu Justyna, Katarzyna Dargelos, Alain Chrostowska, Anna Pasternak, Beata |
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Keywords | Flash vacuum thermolysis 2-Methylimidazole Photoelectron spectroscopy POLYAZAPENTADIENES EXCITATION-ENERGIES IONIZATION-POTENTIALS APPROXIMATION UV-PHOTOELECTRON SPECTROSCOPY DECOMPOSITION DENSITY-FUNCTIONAL THEORY GAS-PHASE GENERATION ELECTRONIC-STRUCTURE Flash vacuum thermolysis Photoelectron spectroscopy 2-Methylimidazole |
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Snippet | Thermal reactions of N-tert-butyl-(E)-crotonaldimine (1a) and 1,4-di-(tert-butyl)-1,4-diazabuta-1,3-dien (glyoxal-bis-N-tert-butylimine) (1b) under FVT... |
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SubjectTerms | 2-Methylimidazole Activation Bonding Chemical Sciences Chemistry Chemistry, Organic Cleavage Flash vacuum thermolysis Formations Inorganic chemistry Organic chemistry Photoelectron spectroscopy Physical Sciences Pyrroles Radicals Science & Technology Spectroscopy Tetrahedrons |
Title | Unusual reactivity of N-tert-butylimines under FVT conditions |
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