84-95-7Relevant articles and documents
Conformational Studies by Dynamic NMR. 35. Structure, Conformation, and Stereodynamics of Hindered Naphthylamines
Casarini, D.,Foresti, E.,Lunazzi, L.,Macciantelli, D.
, p. 4527 - 4532 (1988)
The low-temperature 1H and 13C NMR spectra of a number of N-ethyl- and of N-isopropyl-N-alkyl-1-naphthylamines allowed the measurement of the interconversion barriers between the two twisted enantiomeric conformers.The free energyes of activation increased substantially with the dimension of the N-alkyl groups (e.g., δG**173 is 8.3 Kcal mol-1 when N-alkyl is a methyl group, and δG**373 is 19.85 Kcal mol-1 when N-alkyl is a tert-butyl group in N-ethyl-N-alkyl-1-naphthylamines).Nuclear Overhauser enhancement (NOE) experiments confirmed that these molecules adopt a twist conformation and indicated that in N-methyl as well as in N-ethyl-N-isopropyl-1-naphthylamines the N-isopropyl moiety is closer to H-8 than to H-2.Thes results, obtained in solution, were confirmed by the X-ray investigation of an analogous derivative in the solid state.On the other hand, the less hindered secundary 1-naphthylamines turned out to be planar in solution (NOE experiments) as well as in the solid state (X-ray diffraction).Finally it was found that electron-releasing (e.g., -NH2) and electron attracting (e.g., -NO2) substitunets in position 4 increase and reduce, respectively, the interconversion barriers of the twisted tertiary 1-naphthylamines.As expected this trend is opposite to that reported in the case of planar N-methylanilines containing analogous substituents in position 4.
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Smith
, p. 182 (1882)
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Synthesis of Arylamines via Aminium Radicals
Svejstrup, Thomas D.,Ruffoni, Alessandro,Juliá, Fabio,Aubert, Valentin M.,Leonori, Daniele
supporting information, p. 14948 - 14952 (2017/11/20)
Arylamines constitute the core structure of many therapeutic agents, agrochemicals, and organic materials. The development of methods for the efficient and selective construction of these structural motifs from simple building blocks is desirable but stil
CuI/DMPAO-catalyzed N-arylation of acyclic secondary amines
Zhang, Yu,Yang, Xinye,Yao, Qizheng,Ma, Dawei
supporting information; experimental part, p. 3056 - 3059 (2012/07/28)
DMPAO has been found to be a powerful ligand to enable copper-catalyzed coupling of aryl halides with aliphatic acyclic secondary amines take place under relatively mild conditions, and coupling of aryl halides with primary amines and cyclic secondary amines proceeds at low catalyst loading.
