74650-16-1

Upstream product

• 135286-04-3 β-hydroxy-N-(4-nitrophenyl)phenethylamine 
• 135285-97-1 2-((4-nitrophenyl)amino)-2-phenylethan-1-ol 
• 100-42-5 styrene 
• 1516-60-5 4-nitrophenyl azide 
• 100-01-6 4-nitro-aniline 
• 96-09-3 styrene oxide 
• 6814-64-8 methylenedimethyl sulfurane 
• 785-81-9 4-nitro-N-(phenylmethylene)benzenamine 

Downstream Products

• 1428448-70-7 3-(4-nitrophenyl)-4-phenyloxazolidin-2-one 
• 1428448-71-8 3-(4-nitrophenyl)-5-phenyloxazolidin-2-one 

Relevant academic research and scientific papers

A Metal-Free Synthesis of N-Aryl Oxazolidin-2-Ones by the One-Pot Reaction of Carbon Dioxide with N-Aryl Aziridines

The cost-effective TPPH2/TBACl-catalyzed (TPPH2=dianion of tetraphenyl porphyrin; TBACl=tetrabutyl ammonium chloride) carbon dioxide cycloaddition to N-aryl aziridines was successful in synthesizing N-aryl oxazolidin-2-ones. A cataly

[FeIII(F20-tpp)Cl] Is an effective catalyst for nitrene transfer reactions and animation of saturated hydrocarbons with sulfonyl and aryl azides as nitrogen source under thermal and microwave-assisted conditions

[FeIII(F20-tpp)Cl] (F20tpp = meso- tetrakis(pentafluorophenyl)porphyrinato dianion) is an effective catalyst for imido/nitrene insertion reactions using sulfonyl and aryl azides as nitrogen source. Under thermal conditions, aziridination of aryl and alkyl alkenes (16 examples, 60-95% yields), sulfimidation of sulfides (11 examples, 76-96% yields), allylic amidation/amination of α-methylstyrenes (15 examples, 68-83% yields), and amination of saturated C-H bonds including that of cycloalkanes and adamantane (eight examples, 64-80% yields) can be accomplished by using 2 mol % [FeIII(F20- tpp)Cl] as catalyst. Under microwave irradiation conditions, the reaction time of aziridination (four examples), allylic amination (five examples), sulfimidation (two examples), and amination of saturated C-H bonds (three examples) can be reduced by up to 16fold (24-48 versus 1.5-6 h) without significantly affecting the product yield and substrate conversion.

Allylic amination and aziridination of olefins by aryl azides catalyzed by CoII(tpp): A synthetic and mechanistic study

CoII(tpp) catalyzes the reaction of aromatic azides (ArN 3) with nonactivated olefins to yield allylic amines or aziridines in moderate-to-good yields. The chemoselectivity of the catalytic reaction is particularly high. Depending on the substrate employed, allylic amines or aziridines can be obtained. The reaction mechanism was investigated, and the reaction proceeds through reversible coordination of the aryl azide to the CoII-porphyrin complex. The often postulated nitrene complex is not an intermediate in this reaction. The kinetics for the allylic amination is first order in azide, Co(tpp), and olefin. For the aziridination, the kinetics is again first order in azide and catalyst, but we observed a first-order dependence of the rate on α-methylstyrene only up to an olefin concentration of 6.9 M. An inhibiting role of the competitively formed 1-(4-nitrophenyl)-5-methyl-5-phenyl-1,2,3-triazoline was identified. The triazoline was shown to reversibly coordinate to Co(tpp), which blocks the free coordination site necessary for the catalytic reaction to proceed, and is it responsible for the catalyst deactivation in the aziridination reaction of α-methylstyrene by 4-nitrophenyl azide. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

The (porphyrin)ruthenium-catalyzed aziridination of olefins using aryl azides as nitrogen sources

Aryl azides have been used as atom-efficient nitrene transfer reagents in the (porphyrin)ruthenium-catalyzed amination of olefins. Several azides, olefins and [Ru(porphyrin)CO] complexes were tested to investigate the scope and limits of the reaction. Quantitative yields and short reaction times were achieved by using terminal olefins and aryl azides bearing electron-withdrawing groups on the aryl moiety. The reactions were influenced by steric factors. Internally disubstituted olefins exhibited a lower reactivity and tri- and tetra-substituted olefins did not react at all. A very high turnover number (TON) for the [Ru(TPP)CO] (TPP = tetraphenylporphyrin dianion) catalyzed amination of α-methylstyrene by p-nitrophenyl azide was obtained. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

A facile synthesis of N-aryl aziridines

Reaction of N-aryl-β-amino alcohols with p-toluenesulphonyl chloride under phase transfer catalytic condition gave the corresponding N-aryl aziridines in good yields, whereas N-alkyl-β-amino alcohol [for e.g., L-ephedrine] gave the corresponding N-tosyl derivative as the major product, along with the expected N-alkyl aziridines in lower yield.

Studies on ?-Sulphuranes : Synthesis of 1,2-Diarylaziridines

Methylenedimethylsulphurane, an unstabilized ?-sulphurane, has been generated in situ and reacted with a range of schiff bases to afford 1,2-diarylaziridines (4a-e) in fair to good yields.