13616-82-5Relevant articles and documents
Synthesis method of substituted thiophenol (by machine translation)
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, (2020/06/09)
The invention provides a method for synthesizing substituted thiophenol, which comprises the following steps of preparing compound V compound and NaHSO3 Or KHHSO3 Reaction synthesis IV compound, compound of formula IV and SO2 Reaction-synthesis III compounds of formula III are passed NaBH in NaOH solution. 4 Of formula II is reduced and the compound of formula II is acidified to give a compound of formula I. The method for synthesizing the substituted thiophenol has the advantages of greenness, high efficiency, easiness in industrial application and the like. (by machine translation)
Copper versus thioether-centered oxidation: Mechanistic insights into the non-innocent redox behavior of tripodal benzimidazolylaminothioether ligands
Martínez-Alanis, Paulina R.,Sánchez Eguía, Brenda N.,Ugalde-Saldívar, Víctor M.,Regla, Ignacio,Demare, Patricia,Aullón, Gabriel,Castillo, Ivan
supporting information, p. 6067 - 6079 (2013/07/05)
A series of Cu+ complexes with ligands that feature varying numbers of benzimidazole/thioether donors and methylene or ethylene linkers between the central nitrogen atom and the thioether sulfur atoms have been spectroscopically and electrochemically characterized. Cyclic voltammetry measurements indicated that the highest Cu2+/Cu+ redox potentials correspond to sulfur-rich coordination environments, with values decreasing as the thioether donors are replaced by nitrogen-donating benzimidazoles. Both Cu2+ and Cu+ complexes were studied by DFT. Their electronic properties were determined by analyzing their frontier orbitals, relative energies, and the contributions to the orbitals involved in redox processes, which revealed that the HOMOs of the more sulfur-rich copper complexes, particularly those with methylene linkers (-N-CH2-S-), show significant aromatic thioether character. Thus, the theoretically predicted initial oxidation at the sulfur atom of the methylene-bridged ligands agrees with the experimentally determined oxidation waves in the voltammograms of the NS3- and N2S2-type ligands as being ligand-based, as opposed to the copper-based processes of the ethylene-bridged Cu+ complexes. The electrochemical and theoretical results are consistent with our previously reported mechanistic proposal for Cu 2+-promoted oxidative C-S bond cleavage, which in this work resulted in the isolation and complete characterization (including by X-ray crystallography) of the decomposition products of two ligands employed, further supporting the novel reactivity pathway invoked. The combined results raise the possibility that the reactions of copper-thioether complexes in chemical and biochemical systems occur with redox participation of the sulfur atom. Copyright
Catalytic kinetic resolution of 5-alkoxy-2(5H)-furanones
Faber, Wijnand S.,Kok, Johan,De Lange, Ben,Feringa, Ben L.
, p. 4775 - 4794 (2007/10/02)
The kinetic resolution of racemic 5-alkoxy-2(5H)-furanones, using a chiral aminoalcohol catalyzed 1,4-addition of arylthiols, was examined. Using various butenolides it was shown that a γ-alkoxy substituent appears to be essential to reach high enantioselectivities whereas electron-donating substituents in the arylthiols also increase the selectivity. Cinchona alkaloids are the preferred catalysts for the kinetic resolution, with quinine and quinidine leading to the most efficient and selective thiol additions. A remarkable dilution effect and a strong dependency on the mode of addition of reactants were observed. Optimization studies are presented of the kinetic resolution of 5-methoxy-2(5H)-furanone 2 resulting in (R)-2 or (S)-2 with enantiomeric excesses exceeding 90%. A mechanism for the quinine (quinidine) catalyzed kinetic resolution is given.
