4028-53-9

Upstream product

• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 100-51-6 benzyl alcohol 
• 138-42-1 p-nitrobenzenesulfonic acid 
• 100-39-0 benzyl bromide 

Downstream Products

• 17377-95-6 benzyl(4-methoxyphenyl)amine 
• 3526-43-0 N-(4-methoxybenzyl)aniline 
• 30904-42-8 p-nitrobenzenesulfonate anion 
• 28965-97-1 4-methoxyanilinium⁽¹⁺⁾ 
• 33334-94-0 N-benzyl-m-nitroaniline 

Relevant academic research and scientific papers

Photooxidation of alkyl 4-nitrophenyl sulfides and sulfoxides. Observation of oxidative C-S bond cleavage and rearrangement reactions

Alkyl 4-nitrophenyl sulfides and sulfoxides undergo a self-photoinduced, singlet oxygen oxidation to produce a variety of products, including sulfonates and carbonyl compounds formed by the oxidative cleavage of the C-S bond of the sulfides and sulfoxides. Structural rearrangements are observed in the resulting carbonyl compounds formed in the oxidative cleavage of the C-S bond in the tert-amyl and 2-phenylethyl sulfides. An overall mechanism is proposed which involves the formation of peroxysulfoxides and peroxysulfones which undergo heterolytic C-S bond cleavage to form ion pairs which recombine to form persulfenates or persulfinates which then undergo photo- and/or thermallyinduced homolytic O-O bond cleavage to form alkoxy and sulfinyl or sulfonyl radicals. The alkoxy radicals undergo β-scission, disproportionation, or recombination with the sulfonyl radical to form the observed products. These C-S oxidative cleavage reactions have only been rarely observed in the earlier studies on the singlet oxygen oxidation studies of dialkyl sulfides, and are attributed, in part, to the presence of the 4-nitro group on the aromatic ring which greatly affects the susceptibility of the sulfur atom of the sulfides and sulfoxides toward nucleophilic attack, and on the reactivity of the peroxysulfoxides and peroxysulfones toward heterolytic cleavage of the O-S bond.

Multiple Structure-Reactivity Relationships for a Menschutkin-type SN2 Reaction

The mechanism of nucleophilic displacement was studied by using three variable systems of ρX, ρY and ρZ obtained from the change of substituents X, Y and Z for the reaction of (Z)-substituted benzyl (X)-benzenesulphonates with (Y)-substituted N,N-dimethylanilines in aceton at 35 deg C.The coefficient of the interaction term, ρXY, has a value of 0.21 which means that bond-making and -breaking are concerted in the SN2 transition state.In the range Z = H to p-NO2, in which the SN2 mechanism is predicted to be dominant, the ρZY value is very large, 0.5, which means that the interaction between Z and Y is very large. ρZX is ca. 0.06 which means that the interaction is small between X and Z.In contrast, in the range Z = H to p-Me, in which the SN1 mechanism is dominant, the ρZY value is nearly zero, indicating no interaction between Z and Y.Changes of substituent effect and interaction terms, ρXY, ρYZ and ρZX are useful tools for distinguishing wrong reaction mechanisms.