32846-68-7

Upstream product

• 10442-39-4 tetra-n-butylammonium cyanide 
• 111278-48-9 C₁₈H₁₄N₂O₂S₂ 
• 108-98-5 thiophenol 
• 80-00-2 4-Chlorophenyl phenyl sulfone 
• 1146-39-0 4-nitrophenyl phenyl sulfone 

Downstream Products

• 27375-45-7 1,4-bis-benzenesulfonyl-benzene 

Relevant academic research and scientific papers

Synthesis of a new monomer for sulfonated poly(arylene ether sulfones)

4-({2,4-Bis[(4-chlorophenyl)sulfonyl]phenyl}thio)benzenesulfonic acid was synthesized based on the scheme suggested from the results of retrosynthetic analysis. This compound is a new monomer for the preparation of sulfonated poly(arylene ether sulfones) used as a solid polymer electrolyte in fuel cells. The structure of the aromatic disulfone containing a sulfo group was suggested based on the data on the influence of chemical structure of structural elements of polysulfone proton-conducting membranes on their operational characteristics.

AN SRN1 APPROACH TO SOME AROMATIC NITRILES VIA DIAZOSULFIDES

Diazosulfides 1 react with excess tetrabutylammonium cyanide in Me2SO under photon (sunlamp) or electron (Pt cathode) stimulation to give the corresponding nitriles.The results are interpreted on the basis of an SRN1 mechanism involving the (phenylthio)azo as nucleofugal group.

A CONVENIENT SRN1 SYNTHESIS OF AROMATIC NITRILES FROM DIAZONIUM SALTS VIA DIAZOSULFIDES

Properly substituted diazosulfides XC6H4-N=N-SPh (1) (either isolated or generated in situ from arenediazonium tetrafluoroborates and sodium benzenethiolate) react with tetrabutylammonium cyanide, in Me2SO under photon or electron stimulation, leading to nitriles XC6H4CN (2).Satisfactory yields of 2, comparable with those of the Sandmeyer reaction, are obtained when X= 3- or 4-CF3, 2-, 3-, or 4-CN, 4-F, 4-MeCO, 3-MeO, 4-NO2, 4-PhCO, and 4-PhSO2.For different reasons, the reaction practically fails as a useful nitrile synthesis when X= H, 4-MeO, 2-, or 3-NO2.The collected evidences agree well with the intervention of an SRN1 mechanism to which diazosulfides 1, given their easy reducibility followed by a prompt fragmentation of the C-N and N-S bonds, are convenient participating substrates.An important consequence of the mechanism involved is the behaviour of bromo and chloro derivatives (1: X= Br, Cl) which lead, through the contemporaneous introduction of two cyano functionalities, to more than satisfactory yields of the corresponding dicyanobenzenes.