781660-23-9

Basic information

• Product Name: N-allyl-4-cyanobenzenesulfonamide
• Synonyms: N-allyl-4-cyanobenzenesulfonamide
• CAS NO: 781660-23-9
• Molecular Weight: 222.268
• Mol File: 781660-23-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: N-allyl-4-cyanobenzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-allyl-4-cyanobenzenesulfonamide(781660-23-9)
• EPA Substance Registry System: N-allyl-4-cyanobenzenesulfonamide(781660-23-9)

Safety Data

• Hazardous Substances Data: 781660-23-9(Hazardous Substances Data)

Upstream product

• 107-11-9 1-amino-2-propene 
• 49584-26-1 p-cyanobenzenesulfonyl chloride 

Downstream Products

• 851461-02-4 dithiocarbonic acid S-{1-[(4-cyanobenzenesulfonylamino)methyl]-5,5-dimethyl-4-oxohexyl} ester O-ethyl ester 
• 851461-10-4 dithiocarbonic acid S-(1-{[acetyl(4-cyanobenzenesulfonyl)amino]methyl}-5,5-dimethyl-4-oxohexyl) ester O-ethyl ester 

Relevant articles and documents

Twofold Radical-Based Synthesis of N, C-Difunctionalized Bicyclo[1.1.1]pentanes

Bicyclo[1.1.1]pentylamines (BCPAs) are of growing importance to the pharmaceutical industry as sp3-rich bioisosteres of anilines and N-tert-butyl groups. Here we report a facile synthesis of 1,3-disubstituted BCPAs using a twofold radical functionalization strategy. Sulfonamidyl radicals, generated through fragmentation of α-iodoaziridines, undergo initial addition to [1.1.1]propellane to afford iodo-BCPAs; the newly formed C-I bond in these products is then functionalized via a silyl-mediated Giese reaction. This chemistry also translates smoothly to 1,3-disubstituted iodo-BCPs. A wide variety of radical acceptors and iodo-BCPAs are accommodated, providing straightforward access to an array of valuable aniline-like isosteres.

Synthesis of substituted 3-arylpiperidines and 3-arylpyrrolidines by radical 1,4 and 1,2-aryl migrations

A route to 3-arylpiperidines and 3-arylpyrrolidines involving radical 1,4- and 1,2-aryl migrations has been explored. For the piperidines, the first route requires a xanthate addition to an N-allylarylsulfonamide, followed by acetylation and treatment with lauroyl peroxide to give the corresponding 1,4-aryl transfer product. This compound can be converted into the desired piperidine derivative following acidic hydrolysis. For the second approach to piperidines, addition of an α-keto xanthate to olefins of type 14 causes 1,2-aryl migration leading to an α,β-unsaturated ester, which can be converted into a piperidine by the action of ammonia or a primary amine and sodium cyanoborohydride. Substituted 3-arylpyrrolidines can be obtained by simply starting with an α-amido substituted xanthate.