7763-73-7Relevant academic research and scientific papers
Catalyst-Free Electrophilic Ring Expansion of N-Unprotected Aziridines with α-Oxoketenes to Efficient Access 2-Alkylidene-1,3-Oxazolidines
Chen, Xingpeng,Huang, Zhengshuo,Xu, Jiaxi
supporting information, p. 3098 - 3108 (2021/05/10)
2-(2-Oxoalkylidene)-1,3-oxazolidine derivatives were synthesized in good to excellent yields regiospecifically through the catalyst-free electrophilic ring expansion of N-unprotected aziridines and the ketene C=O double bond of α-oxoketenes, in situ generated from the microwave-assisted Wolff rearrangement of 2-diazo-1,3-diketones. The ring expansion predominantly underwent an SN1 process and the hydrogen bond decides the (E)-configuration of products. (Figure presented.).
Structure and Reactivity of a Manganese(VI) Nitrido Complex Bearing a Tetraamido Macrocyclic Ligand
Shi, Huatian,Lee, Hung Kay,Pan, Yi,Lau, Kai-Chung,Yiu, Shek-Man,Lam, William W. Y.,Man, Wai-Lun,Lau, Tai-Chu
supporting information, p. 15863 - 15872 (2021/09/30)
Manganese complexes in +6 oxidation state are rare. Although a number of Mn(VI) nitrido complexes have been generated in solution via one-electron oxidation of the corresponding Mn(V) nitrido species, they are too unstable to isolate. Herein we report the isolation and the X-ray structure of a Mn(VI) nitrido complex, [MnVI(N)(TAML)]- (2), which was obtained by one-electron oxidation of [MnV(N)(TAML)]2- (1). 2 undergoes N atom transfer to PPh3 and styrenes to give Ph3P═NH and aziridines, respectively. A Hammett study for various p-substituted styrenes gives a V-shaped plot; this is rationalized by the ability of 2 to function as either an electrophile or a nucleophile. 2 also undergoes hydride transfer reactions with NADH analogues, such as 10-methyl-9,10-dihydroacridine (AcrH2) and 1-benzyl-1,4-dihydronicotinamide (BNAH). A kinetic isotope effect of 7.3 was obtained when kinetic studies were carried out with AcrH2 and AcrD2. The reaction of 2 with NADH analogues results in the formation of [MnV(N)(TAML-H+)]- (3), which was characterized by ESI/MS, IR spectroscopy, and X-ray crystallography. These results indicate that this reaction occurs via an initial "separated CPET"(separated concerted proton-electron transfer) mechanism; that is, there is a concerted transfer of 1 e- + 1 H+ from AcrH2 (or BNAH) to 2, in which the electron is transferred to the MnVI center, while the proton is transferred to a carbonyl oxygen of TAML rather than to the nitrido ligand.
Anomalous nuclear overhauser effects in carbon-substituted aziridines: Scalar cross-relaxation of the first kind
Kuprov, Ilya,Hodgson, David M.,Kloesges, Johannes,Pearson, Christopher I.,Odell, Barbara,Claridge, Timothy D. W.
supporting information, p. 3697 - 3701 (2015/03/18)
Anomalous NOESY cross-peaks that cannot be explained by dipolar cross-relaxation or chemical exchange are described for carbon-substituted aziridines. The origin of these is identified as scalar cross-relaxation of the first kind, as demonstrated by a com
METHOD FOR SYNTHESIZING AN N-UNSUBSTITUTED OR N-SUBSTITUTED AZIRIDINE
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Page/Page column 5, (2010/08/07)
Process for preparing an N-unsubstituted or N-substituted aziridine of the formula which comprises reacting an olefin of the formula I where R1 to R5 are each, independently of one another, hydrogen, a linear or branched alkyl radica
A micellar iodide-catalyzed synthesis of unprotected aziridines from styrenes and ammonia
Varszegi, Csaba,Ernst, Martin,Van Laar, Frederik,Sels, Bert F.,Schwab, Ekkehard,De Vos, Dirk E.
, p. 1477 - 1480 (2008/12/22)
(Chemical Equation Presented) Aziridines from ammonia: Unprotected aziridines are formed from styrenes in one catalytic step. Ammonia is incorporated directly using an aqueous micellar solution containing bleach as oxidant and substoichiometric amounts of
A convenient method for the synthesis of 2-arylaziridines from styrene derivatives via 2-arylethenyl(diphenyl)sulfonium salts
Matsuo, Jun-Ichi,Yamanaka, Hiroyuki,Kawana, Asahi,Mukaiyama, Teruaki
, p. 392 - 393 (2007/10/03)
Styrene derivatives reacted with diphenyl(trifluoromethanesulfonyloxy)sulfonium trifluoromethanesulfonate (1) at low temperature to afford 2-arylethenyl(diphenyl)sulfonium triflates (2). Treatment of 2 with primary amines gave the corresponding 2-arylazir
Determination des pKa et reaction d'ouverture acide de quelques alkyl-2 et aryl-2 aziridines
Lamaty, Gerard,Sanchez, Jean-Yves,Sivade, Andre,Wylde, James
, p. 1261 - 1266 (2007/10/02)
Some 2-para substituted aryl aziridines (with pY = CH3O-, CH3-, H-, and Cl-) have been prepared.Their ring opening reaction in acidic medium has been studied and compared with those of two aliphatic aziridines : 2 methyl- and 2,2 dimethyl-aziridine.In aqueous solvent, the addition of HCl, HBr, and HI to the aromatic aziridines leads exclusively to the secondary halogen product, due to the nucleophilic attack on the benzylic carbon.The hydrolysis reaction competes with the addition reaction and is very important for the para methoxy 2-phenyl aziridine.In ethyl alcohol (anhydrous solvent), the hydrohalogenation reaction leads exclusively to halogeno amine with a secondary halogen.The solvolysis reaction, leading to amino-ether, is far less important than in water (excepted for the para methoxy 2-phenyl aziridine).In both solvents, the importance of the solvolysis depends on the HX concentration, as well as the nucleophilic strength of the halogen.The pKa values of these aziridines have been measured, as well as those of 2-phenyl 1-amino 2-ethanol.A linear plot is obtained for the pKa versus ?+p of Brown ; the slopes are respectively -2.8 and 0.Therefore the aromatic aziridines seem to have a behavior similar to that of anilines.
