236122-14-8

Basic information

• Product Name: Aziridine, 2-phenyl-1-[[2-(trimethylsilyl)ethyl]sulfonyl]-
• CAS NO: 236122-14-8
• Molecular Formula: C13H21NO2SSi
• Molecular Weight: 283.467
• Mol File: 236122-14-8.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Aziridine, 2-phenyl-1-[[2-(trimethylsilyl)ethyl]sulfonyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Aziridine, 2-phenyl-1-[[2-(trimethylsilyl)ethyl]sulfonyl]-(236122-14-8)
• EPA Substance Registry System: Aziridine, 2-phenyl-1-[[2-(trimethylsilyl)ethyl]sulfonyl]-(236122-14-8)

Safety Data

• Hazardous Substances Data: 236122-14-8(Hazardous Substances Data)

Upstream product

• 125486-96-6 2-(trimethylsilyl)ethanesulfonamide 
• 100-42-5 styrene 
• 106018-85-3 2-trimethylsilanyl-ethanesulfonyl chloride 
• 593-71-5 Chloroiodomethane 
• 236122-13-7 2-(trimethylsilyl)-N-(phenyl-λ³-iodanylidene)-ethanesulfonamide 

Downstream Products

• 1499-00-9 2-phenylaziridine 

Relevant articles and documents

Iron-catalyzed aziridination reactions

A small quantity of iron(II) triflate (2.5 to 5 mol%) catalyzes the aziridination reactions of enol silyl ethers with tosylimino(iodo)benzene (PhINTs) in acetonitrile to give α-N-tosylamido ketones by subsequent aziridine ring opening. Olefins are convert

Asymmetric N1 unit transfer to olefins with a chiral nitridomanganese complex: Novel stereoselective pathways to aziridines or oxazolines

Chiral nitridomanganese complex 1 was found to be a highly potential N1 unit source for the asymmetric synthesis of aziridines and 2-oxazolines from olefins such as styrene and its derivatives. When sulfonyl chlorides were employed as activators of the complex in the presence of pyridine, pyridine N-oxide, and a silver salt, the reaction of olefins with complex 1 proceeded smoothly to afford the N-sulfonylated aziridines. The aziridination of styrene derivatives with complex 1 using 2-trimethylsilylethanesulfonyl chloride (SESC1) gave the N-SES-aziridines, which were easily converted into chiral N-unsubstituted aziridines. It was found that the reaction was applicable to the asymmetric synthesis of 2-oxazolines from olefins when acyl chlorides were employed as activators. Complex I provided an effective asymmetric environment for trans-disubstituted styrenes in the reaction (up to 92% ee). This is the first example of a direct asymmetric synthesis of 2-oxazolines from olefins. Additional experiments, conducted during the course of this investigation, suggest that the isomerization of the N-acylaziridine intermediate is involved in this reaction.

Copper-catalyzed nitrogen transfer mediated by iodosylbenzene PhI=O [2]

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