97462-61-8

Upstream product

• 100-46-9 benzylamine 
• 50-00-0 formaldehyd 
• 17150-62-8 N-benzyl-3-butenylamine 
• 108-98-5 thiophenol 

Downstream Products

• 97462-62-9 N-(3-butenyl)-N-methylbenzenemethanamine 

Relevant academic research and scientific papers

Utilization of Phenylthio Substituted Amines for the Synthesis of Pyrrolidines

α-Phenylthio substituted amines have been found to be convenient reagents for the preparation of the pyrrolidine ring.Benzylamine (2) undergoes 1,3-dipolar cycloaddition with several dipolarophiles in the presence of silver fluoride.The reaction is believed to proceed via the intermediacy of an azomethine ylide.Treatment of α-(phenylthio)cyanoamines 10 and 17 with strong base results in the loss of the phenylthio group, and formation of substituted trans-piperazines 21, 22 in the case of 17.The mechanism of the reaction involves dimerization of the initially formed cyano substituted azomethine ylide intermediate, which behaves as a captodative diradical.Finally, the reaction of several alkenylamines with tributyltin hydride was studied as a method for generating the pyrrolidine ring via a radical cyclization reaction.

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.