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

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

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

Harnessing Energy-Transfer in N-Centered Radical-Mediated Synthesis of Pyrrolidines

Atom transfer radical addition (ATRA), cyclization (ATRC), and polymerization (ATRP) are valuable synthetic methods for the functionalization of olefins. With the advent of photoredox catalysis, visible-light became a popular tool for the initiation of these reactions. We have developed a protocol that enables easy access to distally functionalized pyrrolidines employing blue-light mediated atom transfer radical [3+2] cyclization. The reaction is scalable, proceeds at very mild conditions. tolerates various functional groups, and provides the corresponding products in good to excellent yields. If rigid olefins are utilized as the reaction partners, the products can be isolated as single diastereomers. The mechanistic investigations provide strong support for an energy-transfer mechanism.

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.

Synthesis of 3-arylpiperidines by a radical 1,4-aryl migration

(Chemical Equation Presented) A route to 3-arylpiperidines, 3-arylpyridines, and 5-arylpiperidin-2-ones involving a radical 1,4-aryl migration has been explored. The sequence requires a xanthate addition to an N-allylarylsulfonamide, followed by acetylation and treatment with dilauroyl peroxide to give the 1,4-aryl transfer product, which upon acidic hydrolysis affords the desired piperidine derivative.