97462-65-2

Upstream product

• 97462-63-0 N-(3-butenyl)-N-((phenylthio)methyl)benzenesulfonamide 
• 106-52-5 N-methyl-4-hydroxypiperidine 
• 98-09-9 benzenesulfonyl chloride 
• 91012-34-9 N-(but-3-en-1-yl)-4-methylbenzenesulfonamide 
• 97462-66-3 N-2-propenyl-N-(2'-bromoethyl) benzene sulphonamide 

Relevant academic research and scientific papers

Radical cyclization as an approach toward the synthesis of pyrrolidines

Free radical cyclizations of several bromo allyl and diallyl substituted sulfonamides are described. The regiochemical course of these cyclizations depend on the nature of the substituent groups attached to the π-bond.

A visible-light photoinduced charge-transfer complex promoted the ring opening of: N-alkyl-4-piperidinols

A visible-light photoinduced ring opening of N-alkyl-4-piperidinols under mild conditions has been achieved. The reaction sequence involves a visible-light-induced charge-transfer complex, which promoted the S-Cl bond cleavage of sulfonyl chlorides. The generated sulfonyl radical further reacts with N-alkyl-4-piperidinol cation radicals to achieve C-N and C-C bond cleavages to yield homoallylamine products.

Synthesis of the Pyrrolidine Ring System by Radical Cyclization

A series of bromo-substituted allyl- and diallyl-substituted sulfonamides have been found to undergo free radical cyclization when treated with tri-n-butyltin hydride in the presence of AIBN.The regiochemical course of the cyclization depends on the nature of the substituent groups attached to the ?-bond.The stereoelectronic factors governing the cyclization reaction of these N-allylsulfonamides are even more stringent than those which occur with the simple 5-hexenyl system.This is probably related to the shorter C-N bond distance which promotes the 5-exo trigcyclization pathway.The present method provides an attractive entry to the preparation of pyrrolidines from easily available N-(2-bromoethyl)-N-allyl- and N-(2-bromopropenyl)-N-allylsulfonamides.The method represents a clear-cut example of the use of hetero-substituted radicals in C-C bond-forming processes.