92568-45-1

Upstream product

• 14677-67-9 phenyl-picryl sulfone 
• 1849-36-1 para-nitrobenzenethiol 
• 55526-39-1 pyrrolidinium 
• 17523-59-0 piperidinium cation 
• 16999-97-6 N-butylammonium cation 
• 88-88-0 2,4,6-trinitrochlorobenzene 

Downstream Products

• 55526-39-1 pyrrolidinium 
• 77379-02-3 2,4,6-trinitro-1-pyrrolidinobenzene 
• 1849-36-1 para-nitrobenzenethiol 
• 17523-59-0 piperidinium cation 
• 67263-27-8 2,4,6-trinitro-1-piperidinobenzene 
• 32902-85-5 N-butyl-2,4,6-trinitroaniline 
• 16999-97-6 N-butylammonium cation 

Relevant academic research and scientific papers

Kinetic Studies of the Reactions of Some Phenyl Aryl Sulfides with Aliphatic Amines in Dimethyl Sulfoxide: the Mechanism of Base Catalysis

The reaction of n-butylamine, pyrrolidine and piperidine with 4'-R-phenyl 2,4,6-trinitrophenyl sulfides (R = H, Me, Br, NO2), 4a-d, result in the rapid formation of ?-adducts by attack at the unsubstituted 3-position; rate and equilibrium data are reported and substituent effects examined. Attack by amine at the 1-position of of 4a-d, phenyl 2,4-dinitronaphthyl sulfide 9, and phenyl 2,6-dinitro-4-trifluoromethyl sulfide 11, results in displacement of the phenylthio group.The substitutions by butylamine show a first order dependence on the amine concentration indicating that nucleophilic attack is rate determining.However the substitutions by pyrrolidine are subject to general base catalysis and it is argued that here the rate limiting step is deprotonation of the initially formed zwitterionic intermediate.

Kinetic and Equilibrium Studies of ?-Adduct Formation and Nucleophilic Substitution in the Reactions of Hydroxide Ions with 2,4,6-Trinitrophenyl Sulfides and Ethers

Kinetic and equlibrium data are reported for reaction of hydroxide ions in 20/80 DMSO/water (v/v) with a series of 4'-substituted phenyl 2,4,6-trinitrophenyl sulfides, 1, and with ethyl thiopicrate, 2, ethyl picrate, 3, phenyl picrate, 4, and 1,3,5-trinitrobenzene, 5.In each case a rapid reaction is observed involving reversible hydroxide addition at an unsubstituted ring-position.In the case of 1-4 this is followed by slower, irreversible attack at the 1-position leading to the formation of picric acid.The Hammett ρ value for equilibrium addition of hydroxide to the 3-position of 1 is 0.98, and the ρ value for rate constants for attack at the 1-position is 0.62.The results are discussed in terms of the electronic and steric effects of the 1-substituents.Comparison of 1-5 indicates that changing from an OR to SR group introduces additional steric crowding.However for the reactions studied changing from R = Et to R = Ph has little steric consequence.