81095-45-6

Upstream product

• 930-69-8 sodium thiophenolate 
• 81064-10-0 2,3-bis(phenylsulphonyl)-1,4-dimethylbenzene 
• 108-98-5 thiophenol 
• 4670-62-6 tetra-N-butylammonium benzenethiolate 
• 74157-74-7 1,4-dimethyl-2-nitro-3-(phenylsulfonyl)benzene 

Downstream Products

• 81064-10-0 2,3-bis(phenylsulphonyl)-1,4-dimethylbenzene 
• 2548-26-7 2,5-dimethyldiphenyl sulfone 
• 81064-14-4 1,4-dimethyl-2-(phenylsulfonyl)-3-<(2,4,6-trimethylphenyl)thio>benzene 

Relevant academic research and scientific papers

Normal SNAr, Telesubstitution, and Electron-Transfer Pathways in the Reactions of Methyl-Substituted o-Bis(phenylsulfonyl)benzene Derivatives with Sodium Arenethiolates in Dimethyl Sulfoxide

1,4-Dimethyl-2,3-bis(phenylsulfonyl)-(6a) and 1,2-bis(phenylsulfonyl)-3,4,5,6-tetramethylbenzene (6b) react with sodium benzenethiolate or 2,4,6-trimethylbenzenethiolate in Me2SO at 120 deg C to give mainly products (7a,b,9, and 10a) resulting from the no

Electrochemical Reduction of Some o-Bis(phenylsulphonyl)benzene Derivatives. Effect of the Substrate Structure and of the Addition of Bases on the Product Distribution.

A study of the electrochemical behaviour of the o-bis(phenylsulphonyl)benzene derivatives (1a-e) in dimethyl sulphoxide containing 0.1M-tetrabutylammonium tetrafluoroborate has been undertaken.The results from cyclic voltammetry, controlled-potential electrolysis, and coulometry strongly argue in support of a mechanism involving initial formation of the radical anion (1)-. which fragments into the ? radical (2) and PhSO2-.Competing pathways for (2) are (a) intramolecular homolytic arylation eventually leading to dibenzothiophene (4) together with dihydrodibenzothiophene (5) derivatives and (b) hydrogen-atom transfer leading to monosulphones (6).The fact that compounds (1a,b) undergo mainly cyclization, whereas the hydrogen-atom transfer predominates in the case of compounds (1c,d), indicates that the structure of the starting substrate is a major governing factor for the above competition.An explanation, based on a concomitance of steric effects of the methyl groups ortho to the phenylsulphonyl substituents, is given.Experiments carried out in the presence of different bases show that the intramolecular arylation leading to the cyclized product can occur also through an unprecedented chain mechanism whose efficiency, which increases as the strength and the concentration of the base is increased, is found in turn to be dependent on the substrate structure.Finally, when arenethiolates are used as bases, a third pathways (the nucleophile-radical coupling step of the SRN1 process) is found to compete for the intermediate ? radical (2) eventually leading to sulphides resulting from the overall substitution of an arylthio for a moiety in (1).When the intramolecular cyclization does not compete efficiently almost quantitative yields of sulphides are obtained via an SRN1 route.

Photostimulated Reactions of o-Bis(phenylsulfonyl)benzene Derivatives with Sodium Arenethiolates in Me2SO. Evidence for Competing Pathways Involving a Common Intermediate ? Radical

The effects of incremental additions of benzenethiol on the product distribution of the photostimulated reactions of 2,3-bis(phenylsulfonyl)-1,4-dimethyl- (1a) and 1,2-bis(phenylsulfonyl)-3,4,5,6-tetramethylbenzene (1b) with sodium benzenethiolate in Me2S

Electrochemical Evidence for an Unusual Base-Catalysed Chain Mechanism in an Intramolecular Homolytic Arylation

Cyclic voltammetry and controlled-potential electrolysis of the disulphone (1a) in dimethyl sulphoxide show that its transformation into the dibenzothiophene dioxide (2a), in the presence of a base, is an efficient electrocatalytic process.