5774-49-2Relevant academic research and scientific papers
α,β-Aziridinylphosphonates by lithium amide-induced phosphonyl migration from nitrogen to carbon in terminal aziridines
Hodgson, DaviD. M.,Xu, Zhaoqing
, p. 978 - 983 (2010)
N-Phosphonate terminal aziridines undergo lithium 2,2,6,6- tetramethylpiperidide-induced N-to C-[1,2]-anionic phosphonyl group migration under experimentally straightforward conditions, to provide a stereocontrolled access to synthetically valuable trans-
Lithiation-induced migrations from nitrogen to carbon in terminal aziridines
Hodgson, David M.,Humphreys, Philip G.,Xu, Zhaoqing,Ward, John G.
, p. 2245 - 2248 (2008/02/14)
(Chemical Equation Presented) Benefiting from deprotection: Lithium 2,2,6,6-tetramethylpiperidide induces N-Boc or N-phosphonate terminal aziridines to undergo regio- and stereoselective N-to-C migration of the protecting group, giving synthetically valua
Synthesis of primary sec-alkylamines via nucleophilic ring-opening of N-phosphorylated aziridines
Gajda, Tadeusz,Napieraj, Anna,Osowska-Pacewicka, Krystyna,Zawadzki, Stefan,Zwierzak, Andrzej
, p. 4935 - 4946 (2007/10/03)
The novel ring-opening reaction of various 2-alkyl- and 2,2-dimethyl-N-(diethoxyphosphoryl)aziridines (1) and (10) with copper-modified Grignard reagents proceeds regiospecifically at the less hindered carbon. The diethyl N-sec-alkylphosphoramidates (2) thus obtained may efficiently be converted to primary sec-alkylamine hydrochlorides (3) by refluxing with 20% hydrochloric acid. 2,3-Disubstituted N-phosphorylated aziridines except N-phosphorylated cyclohexenimine (4) do not react under the described conditions. Copper-mediated reaction of 2-phenyl-N-(diethoxyphosphoryl)aziridine (7) with Grignard reagents affords a mixture of regioisomers (8) and (9) but still with the preference of ring-opening at the carbon of lesser substitution.
