82244-59-5Relevant academic research and scientific papers
Reduction of permanganate by thioanisole: Lewis acid catalysis
Xie, Ning,Binstead, Robert A.,Block, Eric,Chandler, W. David,Lee, Donald G.,Meyer, Thomas J.,Thiruvazhi, Mohan
, p. 1008 - 1015 (2000)
The oxidation of sulfides and sulfoxides by permanganate in anhydrous acetone solutions is catalyzed by Lewis acids such as iron(III) chloride, zinc chloride, and mercury(II) chloride. The reaction kinetics unequivocally confirm that the function of these catalysts is to activate the oxidant by forming permanganate/Lewis acid complexes analogous to the protonation of MnO4/- by Bronsted acids. A Hammett analysis of the rate constants for the oxidation of a series of substituted thioanisoles gives a negative p value (- 1.11) indicative of an electron deficient transition state. No secondary kinetic isotope effect is observed when the hydrogens of the methyl group are replaced by deuterium. Despite previous observations that sulfoxides are preferentially oxidized in competitive experiments, sulfides are oxidized more rapidly when individual rates are measured. All of these observations are most consistent with a mechanism in which the reductant reacts with the oxidant via initial ligation.
Visible-light-promoted cross-coupling reactions of aryldiazonium salts with S-methyl-D3 sulfonothioate or Se-methyl-D3 selenium sulfonate: Synthesis of trideuteromethylated sulfides, sulfoxides, and selenides
Wang, Shun-Yi,Huang, Cheng-Mi,Li, Jian,Ai, Jing-Jing,Liu, Xin-Yu,Rao, Weidong
supporting information, p. 9128 - 9132 (2020/12/02)
A novel visible-light-photocatalytic deuterated thiomethylation/methylselenation of aryldiazonium salts utilizing S/ Se-methyl-d3 sulfonothioate has been developed. The mild conditions and the various functional groups provide a green protocol for the efficient and rapid introduction of the S-CD3 or Se-CD3 group with useful levels of deuterium content (>91% D). Trideuteromethyl sulfoxides have also been successfully chemoselectively observed by simple atmospheric changes under photocatalytic conditions.
Reduction of CO2 with NaBH4/I2 for the Conversion of Thiophenols to Aryl Methyl Sulfides
Zhang, Bo,Fan, Zhengning,Guo, Zhiqiang,Xi, Chanjuan
, p. 8661 - 8667 (2019/07/03)
We report a tandem reaction to realize reduction of carbon dioxide with thiophenols to generate aryl methyl sulfides under the NaBH4/I2 system with 18-crown-6 as the solvent. Thiophenols bearing electron-donating and electron-withdrawing groups are feasible in this reaction. Controlled experiment results indicate that 18-crown-6 plays a critical role in six-electron reduction of carbon dioxide.
