116905-62-5

Basic information

• Product Name: cis-N-tosyl-2-methyl-3-n-propylaziridine
• CAS NO: 116905-62-5
• Molecular Weight: 253.365
• Mol File: 116905-62-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: cis-N-tosyl-2-methyl-3-n-propylaziridine(CAS DataBase Reference)
• NIST Chemistry Reference: cis-N-tosyl-2-methyl-3-n-propylaziridine(116905-62-5)
• EPA Substance Registry System: cis-N-tosyl-2-methyl-3-n-propylaziridine(116905-62-5)

Safety Data

• Hazardous Substances Data: 116905-62-5(Hazardous Substances Data)

Upstream product

• 7688-21-3 cis-2-hexene 
• 1058-14-6 N-p-tolylsulfonylphosphine imide 
• 4050-45-7 trans-2-hexene 
• 70-55-3 toluene-4-sulfonamide 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 473-34-7 N,N-dichloro-p-toluenesulfonamide 

Relevant articles and documents

Nanocrystalline zinc peroxide mediated unprecedented nitrene transfer: An expeditious access to N-tosylaziridines

An unprecedented zinc peroxide (ZnO2) assisted synthetic strategy is reported for the synthesis of N-tosylaziridines from alkenes by using N-tosyliminotriphenylphosphorane (Ph3PNTs) as a nitrene transfer reagent under mild reaction conditions. The reaction of zinc peroxide with Ph3PNTs yielded a zinc oxaziridine intermediate which subsequently reacts with alkenes to give corresponding N-tosylaziridines in high to excellent yields. The Royal Society of Chemistry 2013.

Aziridination of Alkenes catalysed by Porphyrinirons: Selection of Catalysts for Optimal Efficiency and Stereospecificity

meso-Tetra-arylporphyriniron(III) derivatives catalyse the N-tosylaziridination of aryl-substituted styrenes by tosylimidoiodobenzene, PhINTs, a nitrogen analogue of iodosylbenzene.Three secondary reactions were found to limit the yield of N-tosylaziridination: (i) the formation of toluene-p-sulphonamide, TsNH2, which is presumably derived from hydrolysis of a possible iron-nitrene, Fe=NTs, intermediate, (ii) the conversion of the Fe(TPP)(Cl) (TPP = tetraphenylporphyrin) catalyst into an iron(III) complex where the NTs moiety is inserted into an iron-nitrogen bond of Fe(TPP)(Cl), (iii) an oxidative degradation of the porphyrin catalyst.These secondary reactions were avoided to a great extent by using anhydrous conditions and Fe(TDCPP)(ClO4) (TDCPP = tetrakis-2,6-dichlorophenylporphyrin) as a catalyst instead of Fe(TPP)(Cl) and Fe(TPP)(ClO4).Under these conditions, N-tosylaziridination of styrene, cis- and trans-stilbene, and 1,1-diphenylethylene was performed with yields between 40 and 90percent.Fe(TDCPP)(ClO4) was also found to be the best catalyst for N-tosylaziridination of aliphatic alkenes such as hex-1-ene, cyclo-octene, and cis- and trans-hex-2-enes.Although N-tosylaziridination of the two latter alkenes catalysed by Fe(TPP)(Cl) was not stereospecific, this reaction became stereospecific with Fe(TDCPP)(ClO4) as catalyst.These results show that by a proper choice of the porphyriniron catalyst, relatively good yields of N-tosylaziridination of alkenes by PhINTs can be obtained.As for 1,2-disubstituted aliphatic alkenes, syn addition of the NTs moiety to the double bond takes place.A possible mechanism is presented.