6794-92-9Relevant academic research and scientific papers
New method for the synthesis and the mechanism of formation of 1,2-di- and 1,2,3-trialkyldiaziridines
Kuznetsov,Ovchinnikova,Ananikov,Makhova
, p. 2056 - 2060 (2006)
A new simple approach to the synthesis of 1,2-di-and 1,2,3- trialkyldiaziridines has been developed based on direct chlorination of a mixture of the corresponding aldehyde and an excess of primary aliphatic amine in water. The mechanism of this reaction is proposed and confirmed by quantum chemical calculations at the density functional theory level.
Chiral 1,2-dialkenyl diaziridines: Synthesis, enantioselective separation, and nitrogen inversion barriers
Zawatzky, Kerstin,Kamuf, Matthias,Trapp, Oliver
, p. 156 - 162 (2015/03/04)
Trans-1,2-Disubstituted diaziridines form stable enantiomers at ambient conditions because of the two stereogenic pyramidal nitrogen atoms. Functionalized trans-1,2-disubstituted diaziridines can be utilized as a chiral switching moiety between two enantiomeric states in more complex molecular structures. However, the synthesis of functionalized diaziridines is quite challenging, because of the limited tolerance of reaction conditions that can be applied. Here we present a strategy to make trans-1,2-disubstituted diaziridines accessible as versatile building blocks in C-C-bond formations, i.e., the Heck reaction, and therefore introducing aryl substituents. The synthesis of trans-1,2-dialkenyl diaziridines with terminal alkenyl substituents and their stereodynamic properties are described.
The stereodynamics of 1,2-dipropyldiaziridines
Trapp, Oliver,Sahraoui, Laila,Hofstadt, Werner,Koenen, Werner
experimental part, p. 284 - 291 (2010/12/24)
N-alkylated trans-diaziridines are an intriguing class of compounds with two stereogenic nitrogen atoms which easily interconvert. In the course of our investigations of the nature of the interconversion process via nitrogen inversion or electrocyclic ring opening ring closure, we synthesized and characterized the three constitutionally isomeric diaziridines 1,2-di-n-propyldiaziridine 1, 1-isopropyl-2-n-propyldiaziridine 2, and 1,2-diisopropyldiaziridine 3 to study the influence of the substituents on the interconversion barriers. Enantiomer separation was achieved by enantioselective gas chromatography on the chiral stationary phase Chirasil-β-Dex with high separation factors α (1-isopropyl-2-n-propyldiaziridine: 1.18; 1, 2-diisopropyldiaziridine: 1.24; 100°C 50 kPa He) for the isopropyl substituted diaziridines. These compounds showed pronounced plateau formation between 100 and 150°C, and peak coalescence at elevated temperatures. The enantiomerization barriers ΔG? and activation parameters ΔH? and ΔS? were determined by enantioselective dynamic gas chromatography (DGC) and direct evaluation of the elution profiles using the unified equation implemented in the software DCXplorer. Interestingly, 1-isopropyl-2-n-propyldiaziridine and 1,2-diisopropyldiaziridine exhibit similar high interconversion barriers ?G? (100°C) of 128.3 ± 0.4 kJ mol-1 and 129.8 ± 0.4 kJ mol-1, respectively, which indicates that two sterically demanding substituents do not substantially increase the barrier as expected for a distinct nitrogen inversion process.
Syntheses of 1,2-di- and 1,2,3-trialkyldiaziridines
Kuznetsov, Vladimir V.,Makhova, Nina N.,Dmitriev, Dmitrii E.,Seregin, Victor V.
, p. 116 - 118 (2007/10/03)
The reactions of 1,3,5-trialkylhexahydro-1,3,5-triazines with W-chloroalkylamines resulted in 1,2-dialkyldiaziridines, whereas the reactions of AT-chloroalkylamines or N,N-dichloroalkylamines with an excess of primary aliphatic amines gave 1,2,3-trialkyldiaziridines.
