68820-10-0

Upstream product

• 100-42-5 styrene 
• 1666-13-3 diphenyl diselenide 
• 127-65-1 chloroamine-T 
• 5707-04-0 Phenylselenyl chloride 
• 70-55-3 toluene-4-sulfonamide 
• 24395-14-0 N-(p-tolylsulfonyl)-2-phenylaziridine 
• 14971-39-2 benzeneselenolate ion 
• 20343-90-2 bis(phenylseleno)methane 
• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 

Downstream Products

• 58567-43-4 4-methyl-N-(1-phenyl-allyl)-benzenesulfonamide 
• 206361-12-8 N-Allyl-4-methyl-N-(1-phenyl-2-phenylselanyl-ethyl)-benzenesulfonamide 
• 4809-56-7 N-(1-phenylethyl)-p-toluenesulfonamide 

Relevant academic research and scientific papers

Straightforward and direct access to β-seleno- amines and sulfonylamides via the controlled addition of phenylselenomethyllithium (LiCH2SePh) to imines

The transfer of a α-methyl phenylseleno carbanion to variously functionalized N-aryl and N-sulfonyl imines is reported. The fast selenium-lithium exchange conducted on a diselenoacetal with n-BuLi enables the generation of the attacking homologative nucleophile under chemoselective conditions preserving concomitant potentially sensitive functionalities to the lithiating conditions. Uniformly high yields were observed, thus establishing a valuable and conceptually simple approach to the title compounds.

Regioselective ring-opening of aziridines with diselenides and disulfides using the Zn/AlCl3 system

An efficient Zn/AlCl3-promoted highly regioselective one-pot procedure has been demonstrated for the synthesis of β-amino selenides and sulfides from a variety of diselenides/disulfides and aziridines by reductive cleavage of Se-Se and S-S bond

One-pot synthesis of β-amino/β-hydroxy selenides and sulfides from aziridines and epoxides

Diaryl disulfides and diselenides undergo facile cleavage on treatment with rongalite (sodium hydroxymethanesulfinate) to generate the corresponding thiolate and selenolate species in situ, which effect the ring opening of aziridines and epoxides in a reg

Pyrrolidines from olefins via radical cyclization

2,4-Disubstituted N-tosylpyrrolidines were prepared from olifeins via N- tosylaziridination, benseneselenolate ring-opening and reductive radical cyclization. Azidoselenation of olefins, followed by reduction, N-tosylation, N-allylation and reductive radical cyclization, afforded 3,4-disubstituted N- tosylpyrrolidines.

Amidoselenation of Olefins Using p-Toluenesulfonamide as a Nitrogen Nucleophile

The reaction of olefins, benzeneselenenyl chloride, and p-toluenesulfonamide in the presence of zinc(II) chloride affords N--p-toluenesulfonamides in good to excellent yields.When combined with alkylation on the carbon atom bearing the phenylseleno group thus introduced and subsequent oxidative or reductive removal of the selenium moiety, this reaction can be utilized in the preparation of a wide range of allylic or saturated amides.