14034-63-0

Upstream product

• 1024-41-5 benzyl tosylate 
• 99-09-2 3-nitro-aniline 
• 6749-54-8 1-phenylethyl p-toluenesulfonate 
• 154416-00-9 Toluene-4-sulfonic acid 1-methyl-1-phenyl-ethyl ester 

Downstream Products

• 16239-26-2 N-(3-nitrophenyl)benzamidine 
• 920948-56-7 1-(2-methoxyethyl)-3-(3-nitrophenylamino)pyrrole-2,5-dione 

Relevant academic research and scientific papers

Kinetic Isotope Effects involving Deuteriated Aniline Nucleophiles

Primary and secondary α-deuterium kinetic isotope effects are observed with deuteriated aniline nucleophiles in the SN2 reactions of 1-phenylethyl and benzyl benzenesulphonates, providing evidence in support of the four centre transition state mechanism for the former reaction.

Nucleophilic Substitution Reaction of Cumyl Arenesulfonates with Anilines

The nucleophilic substitution reaction of cumyl arenesulfonate with aniline has been investigated.The reaction in acetonitrile proceeds by the SN2 mechanism with probable frontside nucleophilic attack.The large magnitude of ρXZ (=-0.75) obtained results in an observable sign reversal of ρZ at ?'X = 0.83, with a negative ρZ value for ?X > ?'X.This rather unusual phenomenon can be rationalized by a strong interaction between the nucleophile and leaving group due to their close proximity in the transition state, which in turn is a result of the frontside nucleophilic attack.The reactions in methanol indicate that the SN1 channel competes with the SN2 pathway and ion-pair return is observed when the aniline nucleophhile concentration is low.