Synthesis of aryliminoacetonitriles under FVT conditions or by dehydrogenation of arylaminoacetonitriles: an NMR and UV-photoelectron spectroscopy study |
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Authors: | Stanis?aw Le?niak Anna Chrostowska Dawid Kuc Saïd Khayar ?ukasz Urbaniak |
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Institution: | a Faculty of Chemistry, University of ?ód?, Narutowicza 68, 90-136 ?ód?, Poland b Institut Pluridisciplinaire de Recherche sur l'Environnement et les Matériaux UMR 5254, Université de Pau et des Pays de l'Adour, Hélioparc Pau-Pyrénées, 2, Avenue du Président Angot, 64053 PAU Cedex 9, France |
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Abstract: | The synthesis of (E)-arylimino]-acetonitriles 3 has been described. It was found that the title compounds can be obtained on the three ways, namely by: (i) dehydrogenation of arylaminoacetonitriles 1, (ii) thermal fragmentation of 1-aryl-4-cyano-β-lactams 4 and (iii) retro-ene reaction of (allyl-p-methoxyphenyl-amino)-acetonitrile (7a) under FVT conditions. 1H and 13C NMR spectra of compounds 3, 5 and 6, and all their precursors 1 and 4, were recorded and analysed in detail using chemical shifts δH and δC from GIAO DFT B3LYP/6-31(d) calculations] and J-couplings predicted at the DFT B3LYP/IGLO-II level. Also, UV-photoelectron spectra of 4a,d and 3a,d were measured and analysed considering the theoretical evaluation of their ionisation potentials. |
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