Synthesis of aryliminoacetonitriles under FVT conditions or by dehydrogenation of arylaminoacetonitriles: an NMR and UV-photoelectron spectroscopy study

S. Leśniak , Anna Chrostowska (1) , D. Kuc , M. Maciejczyk , S. Khayar , R.B. Nazarski , Ł. Urbaniak

1 IPREM - Institut des sciences analytiques et de physico-chimie pour l'environnement et les materiaux

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. © 2009 Elsevier Ltd. All rights reserved.

Domaines: Chimie inorganique; Chimie organique

S. Leśniak, Anna Chrostowska, D. Kuc, M. Maciejczyk, S. Khayar, et al.. Synthesis of aryliminoacetonitriles under FVT conditions or by dehydrogenation of arylaminoacetonitriles: an NMR and UV-photoelectron spectroscopy study. Tetrahedron, 2009, 65 (51), pp.10581--10589. ⟨10.1016/j.tet.2009.10.080⟩. ⟨hal-01566343⟩