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Article Dans Une Revue Tetrahedron Année : 2013

Unusual reactivity of N-tert-butylimines under FVT conditions

Résumé

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.
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hal-01566325 , version 1 (20-07-2017)

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S. Leśniak, B. Pasternak, K. Justyna, T.Y. Vu, T.K.X. Huynh, et al.. Unusual reactivity of N-tert-butylimines under FVT conditions. Tetrahedron, 2013, 69 (2), pp.722--729. ⟨10.1016/j.tet.2012.10.090⟩. ⟨hal-01566325⟩
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