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Upstream product

• 1774-47-6 trimethylsulfoxonium iodide 
• 783-08-4 [4-(benzylideneamino)phenyl]methanol 
• 593-71-5 Chloroiodomethane 
• 1613-90-7 4-methoxy-N-[(E)-phenylmethylidene]aniline 
• 100-42-5 styrene 
• 2101-87-3 p-methoxy-phenylazide 
• 142415-42-7 methyltetrahydrothiophene triflate 

Downstream Products

• 1623011-96-0 4-methoxy-N-(2-phenyl-2-(2-(pyridin-2-yl)phenyl)ethyl)aniline 

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

Thermal azide-Alkene cycloaddition reactions: straightforward multi-gram access to Δ2-1,2,3-Triazolines in deep eutectic solvents

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.

The asymmetric synthesis of terminal aziridines by methylene transfer from sulfonium ylides to imines

A new ylide-based protocol for the asymmetric aziridination of imines via methylene transfer has been developed involving the use of a simple chiral sulfonium salt and an organic strong base. A systematic study identified triisopropylphenyl sulfonylimines as optimal substrates for the process. Unexpectedly, hindered C2-symmetric sulfonyl salts incorporating bulky ethers at C-2 and C-5-which had previously been useful in the corresponding epoxidation chemistry-decomposed in these aziridination reactions via competing elimination pathways. Under optimised conditions it was found that a simple salt derived from (2R,5R)-2,5-diisopropyl thiolane could mediate asymmetric methylene transfer to a range of imines with uniformly excellent yields with 19-30% ee. Since this is a similar level of enantiomeric excess to that obtained using these same salts in epoxidation chemistry, it was concluded that if more bulky sulfonium salts could be devised which were resistant to decomposition under the reaction conditions, that highly enantioselective aziridine formation by methylene transfer would be possible. The Royal Society of Chemistry.

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 novel procedure for the synthesis of aziridines: Application of Simmons-Smith reagents to aziridination

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.

Ylide Reactions in the Solid State: a Simple Procedure for the Synthesis of Cyclopropanes, Oxiranes and Aziridines

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