147054-74-8

Basic information

• Product Name: 1-(p-Tolylsulfonyl)-2,3-diphenylaziridine
• Synonyms: 1-(4-Methylphenylsulfonyl)-2,3-diphenylaziridine;1-(p-Tolylsulfonyl)-2,3-diphenylaziridine;2,3-Diphenyl-1-tosylaziridine
• CAS NO: 147054-74-8
• Molecular Formula: C₂₁H₁₉NO₂S
• Molecular Weight: 349.45
• Mol File: 147054-74-8.mol
• Article Data: 48

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(p-Tolylsulfonyl)-2,3-diphenylaziridine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(p-Tolylsulfonyl)-2,3-diphenylaziridine(147054-74-8)
• EPA Substance Registry System: 1-(p-Tolylsulfonyl)-2,3-diphenylaziridine(147054-74-8)

Safety Data

• Hazardous Substances Data: 147054-74-8(Hazardous Substances Data)

Usage

Chemical structure

Contains a sulfonyl group and an aziridine ring structure.

Physical state

Solid.

Color

White to off-white powder.

Solubility

Insoluble in water, soluble in organic solvents.

Usage

Commonly used as a building block in organic synthesis.

Applications

Used in the production of pharmaceuticals and agrochemicals.

Reactivity

Utilized as a reagent in the formation of carbon-carbon and carbon-nitrogen bonds in organic reactions.

Field of interest

Has potential applications in the field of medicinal chemistry and drug discovery.

Safety

Should be handled and used with care due to potential health and environmental hazards.

Upstream product

• 473-34-7 N,N-dichloro-p-toluenesulfonamide 
• 588-59-0 stilbene 
• 645-49-8 cis-stilben 
• 908094-04-2 phenyldiazomethane 
• 51608-60-7 phenyl N-tosyl imine 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 70-55-3 toluene-4-sulfonamide 
• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 127-65-1 chloroamine-T 
• 41085-71-6 bromamine T 
• 1058-14-6 N-p-tolylsulfonylphosphine imide 
• 75-18-3 dimethylsulfide 
• 1170303-32-8 N-benzylidene-toluene-p-sulphonamide 

Downstream Products

• 93172-47-5 (+/-)-N-<1,2-diphenylethyl>toluene-p-sulfonamide 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 1269423-58-6 N-(2-methoxy-1,2-diphenylethyl)-4-methylbenzenesulfonamide 
• 3316-42-5 N-(2-hydroxy-1,2-diphenylethyl)-4-methylbenzenesulfonamide 

Relevant articles and documents

Additions of stabilised and semi-stabilised sulfur ylides to tosyl protected imines: Are they under kinetic or thermodynamic control?

Sulfur ylides react with imines, via betaines, to give aziridines. We sought to determine whether betaine formation was reversible in reactions of benzyl-, amide- and ester-stabilised ylides by carrying out cross-over experiments. Thus, the intermediate betaines were generated independently from the corresponding sulfonium salt in the presence of a more reactive imine (p-nitrobenzaldimine). It was found that no incorporation of the more reactive imine was observed in reactions with the benzyl-stabilised ylide, whilst >80% incorporation of the p-nitrobenzaldimine was observed from the ester- and amide-stabilised ylides. These results indicate that benzyl-stabilised ylides react irreversibly with imines but ester- and amide-stabilised react reversibly. Thus, the stereocontrolling step of the process is dependent on the type of ylide employed and the results are used to account for the different diastereoselectivities observed with the different ylides.

A facile C-arylation of N-tosyl aziridines via Ag(I) catalysis

N-Tosyl aziridines react with a variety of arenes and heteroarenes in the presence of 1-2% of silver hexafluorophosphate at room temperature to afford the corresponding β-aryl amine derivatives in excellent yields and with high regioselectivity.

Chiral bis(pyrazolyl)methane copper(I) complexes and their application in nitrene transfer reactions

In this study, chiral bis(pyrazolyl)methane copper(I) acetonitrile complexes were applied to generate two novel terminal copper tosyl nitrene complexes with the nitrene generating agent SPhINTs in dichloromethane at low temperatures. The syntheses of the chiral bis(pyrazolyl)methane ligands are based on pulegone and camphor, members of the natural chiral pool. The chiral copper(I) acetonitrile complexes were applied as catalysts in the copper nitrene mediated aziridination reaction of different styrene derivatives and the C-H amination of various substrates. The reactions afforded good yields, but low enantiomeric excess under mild conditions. The nitrene species have been characterized with UV/Vis and EPR spectroscopy and the products of the decay by ESI mass spectrometry.

A Dicopper Nitrenoid by Oxidation of a CuICuICore: Synthesis, Electronic Structure, and Reactivity

A dicopper nitrenoid complex was prepared by formal oxidative addition of the nitrenoid fragment to a dicopper(I) center by reaction with the iminoiodinane PhINTs (Ts = tosylate). This nitrenoid complex, (DPFN)Cu2(μ-NTs)[NTf2]2 (DPFN = 2,7-bis(fluorodi(2-pyridyl)methyl)-1,8-naphthyridine), is a powerful H atom abstractor that reacts with a range of strong C-H bonds to form a mixed-valence Cu(I)/Cu(II) μ-NHTs amido complex in the first example of a clean H atom transfer to a dicopper nitrenoid core. In line with this reactivity, DFT calculations reveal that the nitrenoid is best described as an iminyl (NR radical anion) complex. The nitrenoid was trapped by the addition of water to form a mixed-donor hydroxo/amido dicopper(II) complex, which was independently obtained by reaction of a Cu2(μ-OH)2 complex with an amine through a protonolysis pathway. This mixed-donor complex is an analogue for the proposed intermediate in copper-catalyzed Chan-Evans-Lam coupling, which proceeds via C-X (X = N or O) bond formation. Treatment of the dicopper(II) mixed donor complex with MgPh2(THF)2 resulted in generation of a mixture that includes both phenol and a previously reported dicopper(I) bridging phenyl complex, illustrating that both reduction of dicopper(II) to dicopper(I) and concomitant C-X bond formation are feasible.