3400-12-2Relevant academic research and scientific papers
Ring Expansion of Donor-Acceptor Cyclopropane via Substituent Controlled Selective N-Transfer of Oxaziridine: Synthetic and Mechanistic Insights
Ghosh, Asit,Mandal, Subhajit,Chattaraj, Pratim Kumar,Banerjee, Prabal
supporting information, p. 4940 - 4943 (2016/10/18)
A distinctive N-substituent controlled electrophilic N-transfer of oxaziridines with donor-acceptor cyclopropanes in the presence of MgI2 is reported. Contrary to earlier reports, the oxaziridine having bulkier N-substituents can also give N-transferred product instead of the O-transferred one. Interestingly, the oxaziridines having α-H containing N-substituents lead to the pyrrolidine derivatives through [3 + 2] cycloaddition. A mechanistic reasoning for this divergent reactivity is depicted by density functional theory calculations and validated through energy decomposition analysis.
Photochemically-induced C-C bond formation between tertiary amines and nitrones
Itoh, Kennosuke,Kato, Ryo,Kinugawa, Daito,Kamiya, Hideaki,Kudo, Ryuki,Hasegawa, Masayuki,Fujii, Hideaki,Suga, Hiroyuki
supporting information, p. 8919 - 8924 (2015/08/24)
Photoexcited nitrones serve as excellent electron acceptors as well as radical acceptors in the presence of tertiary amines to give β-amino hydroxylamines via photochemically-induced direct sp3 C-H functionalization of the tertiary amines. The combined use of an organophotosensitizer and photoirradiation was highly effective in accelerating addition reactions. Several nitrones and tertiary amines were successfully utilized to give β-amino hydroxylamines in good yield. Highly regioselective generation of primary α-aminoalkyl radicals based on Lewis's stereoelectronic rule and diastereoselective addition reactions of primary α-aminoalkyl radicals with nitrones were successfully achieved. Furthermore, a highly diastereoselective reaction of an α-aminoalkyl radical with a chiral (E)-geometry-fixed α-alkoxycarbonylnitrone was performed.
[Bmim]BF4-immobilized rhenium-catalyzed highly efficient oxygenation of aldimines to oxaziridines using solid peroxides as oxidants
Jain, Suman L.,Singhal, Sweety,Sain, Bir
, p. 2930 - 2935 (2008/02/02)
Various rhenium-based catalysts immobilized in [bmim]BF4 were found to be efficient for oxygenation of various aldimines to the corresponding oxaziridines in excellent yields under mild conditions using solid peroxides like UHP, SPC and SPB as oxidants. Among the various rhenium-based catalysts studied, MTO was found to be most efficient. The reusability and recyclability of MTO immobilized in [bmim]BF4 was established by using it for three subsequent cycles for oxygenation of benzylidine-tert-butylamine using UHP as oxidant.
An environmentally friendly oxidation system for the selective oxygenation of aldimines to oxaziridines with anhydrous TBHP and alumina-supported MoO 3 as a recyclable heterogeneous catalyst
Singhal, Sweety,Jain, Suman L.,Prasad,Sain, Bir
, p. 2051 - 2054 (2008/02/04)
A highly efficient and selective protocol for the oxygenation of various aldimines to oxaziridines, which proceeds in excellent yields with enhanced selectivity by using alumina-supported M0O3 as a recyclable heterogeneous catalyst and anhydrous TBHP as the ultimate oxidant, is described. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Action d'un Tetrafluoroborate d'Oxaziridinium sur les Amines et les Imines
Hanquet, Gilles,Lusinchi, Xavier
, p. 12185 - 12200 (2007/10/02)
The Oxaziridinium salt 1 derived from dihydroisoquinolin is an oxygen transfer reagent to primary amines leading to nitrosoderivatives (if R = Alkyl) or nitro compounds (if R = Aryl), to tertiary amines leading to N-oxides, and to secondary amines and imines leading to the corresponding nitrone.
The Synthesis of NH Aldimines and Derivatives by Spontaneous and Base-catalysed Decomposition of Oxaziridines
Boyd, Derek R.,Coulter, Peter B.,Hamilton, Robert,Thompson, Norris T.,Sharma, Narain D.,Stubbs, Michael E.
, p. 2123 - 2128 (2007/10/02)
A range of oxaziridines containing N-methylene substituents has been synthesized by peracid oxidation of the corresponding fluorenylidene N-alkylamines.Spontaneous and tertiary amine base-catalysed decomposition of the oxaziridines into unstable NH aldimines and derivatives was observed.Acrylaldehyde, 2-methylacrylaldehyde, and benzaldehyde NH imines have been identified as initial products from decomposition of the corresponding oxaziridines. 2,4,6-Trialkylhexahydro-1,3,5-triazines, N,N'-dialkylidene-1,1-diaminoalkanes, N,N'-diarylidene-1,1-diaminoalkanes, and N-isobutylidene-2-methylpropenylamine were among the isolated products formed via the undetected alkyl aldehyde NH imines resulting from oxaziridine decomposition.
