102879-24-3Relevant academic research and scientific papers
Reduction of 2-chloro-N-phenylpropanamide and 2-methyl-N-phenylaziridine with lithium aluminium hydride
Vilhelmsen, Mie Hojer,stergaard, Lars Frosig,Nielsen, Mogens Brondsted,Hammerum, Steen
, p. 1773 - 1778 (2008)
The reduction of 2-chloro-N-phenylpropanamide with LiAlH4 has been re-examined. In contrast to previous findings, we obtain in almost equal quantities two amines from this reaction, namely N-propylaniline and the rearranged product N-isopropylaniline. 2-Methyl-N-phenylaziridine is an intermediate in the reduction and can be isolated from reactions with less LiAlH4. Reduction of 2-methyl-N-phenylaziridine itself proceeds non-regioselectively to provide a mixture of propyl- and isopropylanilines. Formation of the amines by reduction of the aziridine is much slower than formation by reduction of the 2-chloropropanamide, which indicates that Lewis acid catalysis (by aluminium chlorohydrides) facilitates the reduction of the aziridine. In addition, Lewis acid catalysis increases the relative yield of the propylamine product. The reduction of 2-chloro-N-phenylpropanamide furnishes 2-phenylamino-1-propanol as a by-product, rather than the previously proposed 1-phenylamino-2-propanol. The Royal Society of Chemistry.
Direct conversion of epoxides into aziridines with N-arylphosphoramidates
Minicone, Fabrizio,Rogers, Wendy J.,Green, James F.J.,Khan, Mommna,Smith, Geoffrey M.T.,Bray, Christopher D.
, p. 5890 - 5891 (2014/12/12)
Treatment of terminal epoxides with N-arylphosphoramidate anions leads directly to N-aryl aziridines. Existing methods for this transformation employ either multi-step syntheses or an iminophosphorane in conjunction with a Lewis acid. The described method therefore presents an advantage in terms of brevity and atom economy.
