13630-88-1

Upstream product

• 98-10-2 benzenesulfonamide 
• 624-65-7 2-propynyl chloride 

Downstream Products

• 185384-25-2 N-Prop-2-ynyl-N-(3-trimethylsilanyl-prop-2-ynyl)-benzenesulfonamide 
• 138856-01-6 1,7-bis(trimethylsilyl)-4-aza-4-(phenylsufonyl)hepta-1,6-diyne 
• 934972-36-8 N-[3-(1-Hydroxy-2,3-dimethoxy-4-oxo-cyclobut-2-enyl)-prop-2-ynyl]-N-(3-trimethylsilanyl-prop-2-ynyl)-benzenesulfonamide 
• 185384-26-3 N-(2-propynyl)-N-(4-methyl-4-hydroxy-2-pentynyl)benzenesulfonamide 

Relevant academic research and scientific papers

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.