4185-21-1Relevant academic research and scientific papers
New synthesis of diphenyl-N-(substituted)ketenimines from diaminophosphonium diazaylides
Cristau, Henri-Jean,Jouanin, Isabelle,Taillefer, Marc
, p. 68 - 72 (1999)
Diaminophosphonium diazaylides 2 react under mild conditions with diphenylacetyl chloride, to afford diphenyl-N-(substituted)ketenimines 4 or, depending on the case, their transformation products: either the tautomer 8, or the dimer 9. The general reactio
Hydroalumination of Ketenimines and Subsequent Reactions with Heterocumulenes: Synthesis of Unsaturated Amide Derivatives and 1,3-Diimines
Jin, Xing,Willeke, Matthias,Lucchesi, Ralph,Daniliuc, Constantin-Gabriel,Fr?hlich, Roland,Wibbeling, Birgit,Uhl, Werner,Würthwein, Ernst-Ulrich
, p. 6062 - 6075 (2015/06/30)
The series of differently substituted ketenimines 1 was hydroluminated using di-iso-butyl aluminum hydride. For the sterically congested ketenimine 1a, preferred hydroalumination of the C=N-bond was proven by X-ray crystallography (compound 5a). In situ treatment of the hydroaluminated ketenimines 5 with various heterocumulenes like carbodiimides, isocycanates, isothiocyanates and ketenimines as electrophiles and subsequent hydrolytic workup resulted in novel enamine derived amide species in case of N-attack (sterically less hindered ketenimines) under formation of a new C-N-bond or in 1,3-diimines by C-C-bond-formation in case of bulky substituents at the ketenimine-nitrogen atom. Furthermore, domino reactions with more than 1 equiv of the electrophile or by subsequent addition of two different electrophiles are possible and lead to polyfunctional amide derivatives of the biuret type which are otherwise not easily accessible.
Formation of hemiaminals by N-protonation of ketenimines (etheneimines) sterically hindered at carbon
Hegarty, Anthony F.,Kelly, John G.,Relihan, Colette M.
, p. 1175 - 1181 (2007/10/03)
The bis(pentamethylphenyl)-N-isopropyl-ketenimine [N-isopropyl-2,2-bis(pentamethylphenyl)-ethenimine] 11 undergoes pre-equilibrium N-protonation followed by water attack in 1:1 acetonitrile-water at 25°C. This is confirmed by the inverse solvent isotope e
A New and Facile Synthesis of Ketene Imines and Their 2-Iminoazetidine Dimer from Nitriles via Their Nitrilium Salts
Fuks, Robert,Baudoux, Dominique,Piccinni-Leopardi, Carla,Declercq, Jean-Paul,Meerssche, Maurice Van
, p. 18 - 22 (2007/10/02)
A new one-pot synthesis of N-tert-butylketene imines 3 was accomplished on the basis of the reaction of N-tert-butylacetonitrilium tetrachloroferrate 2 with an organic base such as triethylamine or N-trisubstituted amidine 4.The α-hydrogen in 2 is particu
