149818-20-2

Upstream product

• 127-65-1 chloroamine-T 
• 103-26-4 Methyl cinnamate 
• 41085-71-6 bromamine T 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 103-26-4 methyl cinnamate 
• 55962-05-5 4-methyl-N-[(E)-phenyl-λ³-iodanylidene]benzenesulfonamide 

Downstream Products

• 163013-11-4 methyl trans-2-(N-(p-tolylsulfonyl)amino)cinnamate 
• 127053-48-9 Methyl (2R^*,3R^*)-3-phenyl-1H-aziridine-2-carboxylate 
• 124994-24-7 5-isopropenyl-2-phenyl-1-tosyl-3-pyrroline 
• 124994-16-7 cis-3-(3-methyl-1,3-butadienyl)-2-phenyl-1-tosylaziridine 
• 97478-23-4 cis-3-(1,3-butadienyl)-2-phenyl-1-tosylaziridine 
• 97478-38-1 5-ethenyl-2-phenyl-1-tosyl-3-pyrroline 
• 101719-48-6 ethyl 3-(4-methylphenylsulfonamido)-3-phenylpropanoate 
• 97478-49-4 cis-2-formyl-3-phenyl-1-tosylaziridine 

Relevant academic research and scientific papers

Application of the Evans aziridination procedure to 2-substituted acrylates and cinnamates: An expedient route to α-substituted α- and β- amino acids

Reaction of the title compounds with PhI = NSO2Ar (Ar = p-tolyl or p- nitrophenyl) in the presence of catalytic copper (II) triflate in acetonitrile gave the corresponding 2 and/or 3-substituted aziridine-2- carboxylates in generally good yield

Investigations in the transition metal catalyzed aziridination of olefins, amination, and other insertion reactions with Bromamine-T as the source of nitrene

Investigations into the transition metal catalyzed aziridination of olefins with Bromamine-T as a new source of nitrene is presented in this account. Comparison of Chloramine-T and Bromamine-T in this reaction indicates that the latter is superior as the source of nitrene. Systematic study with several transition metal based catalysts suggests that Cu-halides are the best catalysts. A first report of aziridination under microwave and ultrasound irradiation conditions is also presented. Copper-catalyzed aziridination of methyl cinnamate with Bromamine-T did not proceed at ambient temperature but was effected smoothly under ultrasound irradiation to furnish trans-aziridine selectively, while under microwave irradiation, a mixture of cis and trans isomers, was obtained. It has been demonstrated that aziridination of olefins proceeds smoothly with inexpensive bleaching powder. Preliminary results of Rh-catalyzed benzylic insertion reactions with Bromamine-T are included in this account.

TRANSFORMATION OF N-TOSYL-2-(1,3-BUTADIENYL)AZIRIDINE INTO N-TOSYL-2-ETHENYL-3-PYRROLINE.

1,3-Butadienylaziridines or 1,3-butadienylazetidines activated by N-tosyl group smoothly rearrange to vinylpyrroline derivatives or vinylpiperidines in the presence of a catalytic amount of Pd(PPh3)4.Triphenyltin radical induced rearrangement of title compounds is also described.