18713-90-1Relevant academic research and scientific papers
Mild and efficient method for regioselective ring opening of aziridines with amines by bismuth trichloride
Swamy, Navath Raghavendra,Venkateswarlu
, p. 547 - 554 (2007/10/03)
Aziridines undergo the facile ring opening with anilines to afford the 1,2-diamines in excellent yields by bismuth trichloride in acetonitrile at ambient temperature.
Zinc(II)-catalysed transformation of epoxides to aziridines
Kuehnau, Dorte,Thomsen, Ib,Jorgensen, Karl Anker
, p. 1167 - 1170 (2007/10/03)
The Lewis acid-catalysed transformation of epoxides to aziridines with iminophosphoranes as the nitrogen-fragment donor has been investigated. Of the Lewis acids tested, zinc(II) complexes had the best catalytic properties. The method works best for terminal and cyclic epoxides, internal epoxides being less reactive. Of the various iminophosphoranes employed N-(triphenylphosphoranylidene)-aniline and -isopropylamine were the most successful. The zinc(II)-catalysed reaction has been studied for chiral styrene oxides for which the enantiomeric excess of the aziridine produced is dependent on the reaction time. The reaction of achiral and chiral styrene oxides and N-(triphenylphosphoranylidene)aniline in the presence of a zinc(II) complex having a chiral ligand has been investigated as has the reaction for cis-deuteriostyrene oxide in order to obtain information about the stereochemical outcome of the reaction. A mechanism for the title reaction is discussed on the basis of the experimental results.
Organoboranes for synthesis. Reaction of organoboranes with representative organic azides. A general stereospecific synthesis of secondary amines and N-substituted aziridines
Brown, Herbert C.,Midland, M.Mark,Levy, Alan B.,Brown,Wetherill,Suzuki, Akira,Sono, Sunao,Itoh, Mitsuomi
, p. 4079 - 4088 (2007/10/02)
Reaction of trialkylboranes with organic azides in refluxing xylene, followed by hydrolysis, leads to good yields of secondary amines. This reaction is highly dependent on the steric effects around both boron and the azide moiety. The reaction becomes much slower when the steric bulk of one of the reagents is increased and fails when both are hindered. The dialkylchloroboranes are more reactive than trialkylboranes and provide better yields of the desired secondary amines with a11 azides tested. The alkyldichloroboranes react with organic azides at temperatures between room temperature and 60°C and produce excellent yields of secondary amines. Furthermore, the stereochemistry of the original carbon-boron bond is retained. The mechanism of these reactions is discussed and the reaction applied to the synthesis of N-alkyl- and N-arylaziridines.
