21399-96-2Relevant academic research and scientific papers
Ring opening reactions of 2-trialkylsilylaziridines
Bassindale, Alan R.,Kyle, Patricia A.,Soobramanien, Marie-Claire,Taylor, Peter G.
, p. 439 - 448 (2000)
2-Trialkytsilylaziridines do not readily undergo nucleophilic ring opening without electrophilic assistance. In the presence of strong acids protonation at the nitrogen is followed by nucleophitic attack α to the silicon. With non-nucleophilic counterions, the protonated aziridine can be obtained. N-Alkylation gives the aziridinium salt, which also undergoes α-cleavage. However, the presence of a 3-phenyl substituent gives a stable aziridinium salt that undergoes nucleophilic attack β to the silicon. Reaction of 2-trialkylsilylaziridines with trialkylsilyl halides usually leads to α-cleavage, however, desilylation to give the enamine is also observed. Fluorodesilylation of the 2-trialkylsilylaziridine is not straightforward and only occurred readily when a 2-ethoxycarbonyl group was present. Fluorodesilylation followed by attack on a carbonyl was only observed when very dry samples of fluoride ions were employed.
Thermal azide-Alkene cycloaddition reactions: straightforward multi-gram access to Δ2-1,2,3-Triazolines in deep eutectic solvents
Sebest, Filip,Casarrubios, Luis,Rzepa, Henry S.,White, Andrew J. P.,Díez-González, Silvia
supporting information, p. 4023 - 4035 (2018/09/11)
The multi-gram synthesis of a wide range of 1,2,3-Triazolines via azide-Alkene cycloaddition reactions in a Deep Eutectic Solvent (DES) is reported. The role of DES in this transformation as well as the origin of the full product distribution was studied with an experimental/computational-DFT approach.
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.
A lithiomethyl trimethylammonium reagent as a methylene donor
Den Hartog, Tim,Sarria Toro, Juan M.,Couzijn, Erik P. A.,Chen, Peter
supporting information, p. 10604 - 10607 (2014/11/08)
Straightforward deprotonation of soluble tetramethylammonium salts with alkyllithium reagents gives lithiomethyl trimethylammonium reagents. Coordination of the Li cation is crucial to the stability of these 'N-C ylides'. These reagents were used to prepare epoxides, aziridines and allylic alcohols. This journal is the Partner Organisations 2014.
Iron-mediated intermolecular N-group transfer chemistry with olefinic substrates
Hennessy, Elisabeth T.,Liu, Richard Y.,Iovan, Diana A.,Duncan, Ryan A.,Betley, Theodore A.
, p. 1526 - 1532 (2014/03/21)
The dipyrrinato iron catalyst reacts with organic azides to generate a reactive, high-spin imido radical intermediate, distinct from nitrenoid or imido species commonly observed with low-spin transition metal complexes. The unique electronic structure of
Novel aziridination of α-halo ketones: an efficient nucleophile-induced cyclization of phosphoramidates to functionalized aziridines
Yadav, Lal Dhar S.,Rai, Ankita,Rai, Vijai K.,Awasthi, Chhama
, p. 687 - 690 (2008/09/17)
A novel and efficient aziridination of α-halo ketones is reported. The reaction of α-halo ketones with diethyl N-arylphosphoramidates affords diethyl N-aryl-N-(2-oxoalkyl)phosphoramidates which undergo reductive (H--induced) cyclization with so
A novel procedure for the synthesis of aziridines: Application of Simmons-Smith reagents to aziridination
Aggarwal, Varinder K,Stenson, Rachel A.,Jones, Ray V.H.,Fieldhouse, Robin,Blacker, John
, p. 1587 - 1589 (2007/10/03)
The reaction of Simmons-Smith carbenoids with imines in the presence of sulfides provides N-(p-toluenesulfonyl)- and N-[(1,1,1-trimethylsilyl)ethyl]sulfonyl-substituted aziridines in high yield.
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.
Ylide Reactions in the Solid State: a Simple Procedure for the Synthesis of Cyclopropanes, Oxiranes and Aziridines
Toda, Fumio,Imai, Nobuhiro
, p. 2673 - 2674 (2007/10/02)
Treatment of chalcones, cyclohexanones and imines with trimethyloxosulfonium or trimethylsulfonium iodide and KOH in the solid state give cyclopropanes, oxiranes and aziridines, respecively, in good yields.Solid-state methylene transfer also occurs enanti
TRIMETHYLSULFONIUM METHYLSULFATE, A SIMPLE AND EFFICIENT EPOXIDIZING AGENT.
Mosset, Paul,Gree, Rene
, p. 749 - 758 (2007/10/02)
Sulfonium salts 1 and 3 are highly reactive epoxidizing agents under phase transfer catalytic conditions.
