210972-39-7

Upstream product

• 127-65-1 chloroamine-T 
• 107-18-6 allyl alcohol 
• 50487-71-3 4-methyl-N-(2-propenyl)benzenesulfonamide 
• 5997-56-8 4-methyl-N-(oxiran-2-ylmethyl)benzenesulfonamide 
• 75-15-0 carbon disulfide 
• 87301-29-9 N-(phenylsulfonylimino)-phenyl-λ³-iodane 
• 41085-71-6 bromamine T 

Downstream Products

• 865787-94-6 2-(methoxymethyl)-1-(4-methylbenzenesulfonyl)aziridine 
• 223905-86-0 N-(4-methylphenylsulfonyl)-2-<(phenylmethoxy)methyl>aziridine 
• 50487-71-3 4-methyl-N-(2-propenyl)benzenesulfonamide 

Relevant academic research and scientific papers

Synthesis of thiazolidine-thiones, imino-thiazolidines and oxazolidines: Via the base promoted cyclisation of epoxy-sulfonamides and heterocumulenes

Epoxy-sulfonamides react with heterocumulenes (carbon disulfide/isothiocyanates/isocyanates) in the presence of a base to afford ring expansion products in good to high yields with excellent regioselectivity. N-(2-Bromoethyl)-sulfonamides can also be employed as substrates. This reaction proceeds through a 5-exo-tet pathway without forming aziridine intermediates.

M-CPBA-Mediated Intramolecular Aminohydroxylation of N-Sulfonyl Aminoalkenes to Synthesize β-Hydroxyl Cyclic Amines

A variety of structurally diverse N-sulfonyl-protected aminoalkenes readily reacted with m-CPBA to produce a series of β-hydroxyl cyclic amines in high yields through intramolecular aminohydroxylation. This metal-free and easy-to-handle synthetic methodol

Chemo-, regio-, and stereoselective silver-catalyzed aziridination of dienes: Scope, mechanistic studies, and ring-opening reactions

Silver complexes bearing trispyrazolylborate ligands (Tpx) catalyze the aziridination of 2,4-diene-1-ols in a chemo-, regio-, and stereoselective manner to give vinylaziridines in high yields by means of the metal-mediated transfer of NTs (Ts = p-toluensulfonyl) units from PhI=NTs. The preferential aziridination occurs at the double bond neighboring to the hydroxyl end in ca. 9:1 ratios that assessed a very high degree of regioselectivity. The reaction with the silver-based catalysts proceeds in a stereospecific manner, i.e., the initial configuration of the C=C bond is maintained in the aziridine product (cis or trans). The degree of regioselectivity was explained with the aid of DFT studies, where the directing effect of the OH group of 2,4-diene-1-ols plays a key role. Effective strategies for ring-opening of the new aziridines, deprotection of the Ts group, and subsequent formation of β-amino alcohols have also been developed.

Synthesis of substituted allylic sulfonamides from β-alkoxy aziridines and organolithium reagents

The scope and limitations of the organolithium-mediated conversion of β-methoxy N-tosyl aziridines derived from acyclic allylic alcohols into substituted allylic sulfonamides are described. Georg Thieme Verlag Stuttgart.

Palladium(II) mediated aziridination of olefins with bromamine-T as the nitrogen source: scope and mechanism

The palladium(II)-promoted reaction of a variety of olefins and bromamine-T provided N-tosyl-2-substituted aziridines under mild conditions. Olefins bearing chiral appendages gave only a poor to modest diastereoselectivity. Appropriate deuterated olefins

Ring opening and expansion of aziridines in a silica-water reaction medium

Ring-opening reactions of N-tosylaziridines with water-soluble nucleophiles proceeded in a silica-water reaction medium. The system is applicable to a ring expansion of an aziridine with potassium thiocyanate, leading to a thiazolidine derivative.

Lewis base catalyzed ring opening of aziridines with silylated nucleophiles

(Chemical Equation Presented) The ring opening of N-tosylaziridines with trimethylsilylated nucleophiles, catalyzed by N,N,N′,N′- tetramethylethylenediamine, led to the production of β-functionalized sulfonamides in good to excellent yields with high regi

N-bromoamides as versatile catalysts for aziridination of olefins using chloramine-T

N-Bromoamides catalyze effectively the aziridination of electron-deficient as well as electron-rich olefins using chloramine-T (N-chloro-N-sodio-p-toluenesulfonamide) as a nitrogen source under ambient conditions to afford the corresponding aziridines in

Palladium(II)-promoted aziridination of olefins with bromamine T as the nitrogen transfer reagent

The palladium(II)-promoted reaction of a variety of olefins and bromamine T, as the nitrogen atom transfer reagent, provided N-tosyl-2-substituted aziridines under mild conditions.

Pyridinium hydrobromide perbromide: A versatile catalyst for aziridination of olefins using chloramine-T

Formula presented Pyridinium hydrobromide perbromide (PyHBr3) catalyzes effectively the aziridination of electron-deficient as well as electron-rich olefins using Chloramine-T (N-chloro-N-sodio-p-toluenesulfonamide) as a nitrogen source to afford the corr