76745-12-5Relevant academic research and scientific papers
Iron(III) chloride (FeCl3)-catalyzed electrophilic aromatic substitution of chlorobenzene with thionyl chloride (SOCl2) and the accompanying auto-redox in sulfur to give diaryl sulfides (Ar2S): Comparison to catalysis by aluminum chloride (AlCl3)
Sun, Xiaoping,Haas, David,Lockhart, Chyress
, p. 376 - 380 (2017/02/18)
The Lewis acids MCl3(M = Fe and Al)-catalyzed electrophilic aromatic (ArH) substitution reactions with thionyl chloride (SOCl2) have been shown to give diaryl sulfoxide (Ar2SO) and the reduced diaryl sulfide (Ar2S). Under various selected conditions, the FeCl3-catalyzed reactions of chlorobenzene gave substantially much higher percent yields of Ar2S (Ar = p-ClC6H4) than the reactions catalyzed by AlCl3, showing that FeCl3facilitates the reduction in the sulfur center of SOCl2. A dπ?>pπ*back bond between Fe(III) and the O?S group is thought to be responsible for enhancement of the reduction.
Palladium-catalyzed C-S coupling: Access to thioethers, benzo[b]thiophenes, and thieno[3,2-b]thiophenes
Kuhn, Marius,Falk, Florian C.,Paradies, Jan
supporting information; experimental part, p. 4100 - 4103 (2011/10/08)
The first C-S bond formation/cross-coupling/cyclization domino reaction using thiourea as a cheap and easy to handle dihydrosulfide surrogate has been developed. Structurally important biarylthioether, benzo[b]thiophenes, and thieno[3,2-b]thiophene scaffolds are provided in high yield.
Sulfur analogues of polychlorinated dibenzo-p-dioxins, dibenzofurans and diphenyl ethers as inducers of CYP1A1 in mouse hepatoma cell culture and structure-activity relationships
Kopponen,Sinkkonen,Poso,Gynther,Karenlampi
, p. 1543 - 1548 (2007/10/03)
Three sulfur-containing compounds, 2,3,7,8-tetrachlorothianthrene (TCTA), 2,3,7,8-tetrachlorodibenzothiophene (TCDT), and 3,3',4,4'- tetrachlorodiphenyl sulfide (TCDPS), were analyzed for their CYP1A1-inducing potencies - measured as aryl hydrocarbon hydroxylase (AHH) and 7- ethoxyresorufin O-deethylase (EROD) activities - in mouse hepatoma cell culture Hepa-1. Marked differences in the induction potencies were observed among the three compounds studied and between 2,3,7,8-tetrachlorodibenzo-p- dioxin (TCDD) and its sulfur analogue. The estimated EC50 values for TCDD, TCTA, and TCDT were about 8 pM, 700 pM, and 7.5 nM, respectively. TCDPS did not elicit any AHH/EROD induction. Comparative molecular field analysis (CoMFA) was not able to predict correctly the biological potency of TCTA and TCDT. The most important reason for the poor performance of the model may be the positive point charge of sulfur in TCTA and TCDT.
