111-31-9Relevant articles and documents
A practical, one-step synthesis of primary thiols under mild and neutral conditions using bis(triorganotin) sulfides
Gingras,Harpp
, p. 1397 - 1400 (1990)
Thiols are obtained from primary organic halides and bis(triaryl/alkyltin) sulfides in the presence of fluoride ion in CH3CN/H2O at 20°C. This simple one-step methodology involving fluorodestannylation is carried out under mild and neutral conditions, in sharp contrast to virtually all known methods. Some attempts at utilizing triorganotin and triorganogermanium mercaptans for the same purpose are reported.
Reaction mechanisms of thioetherification for mercaptans and olefins over sulfided Mo-Ni/Al2O3 catalysts
Shen, Zhibing,Ke, Ming,Yu, Pei,Hu, Haiqiang,Song, Zhaozheng,Jiang, Qingzhe
, p. 120 - 127 (2015)
The thioetherification reaction of 1-butanethiol and 1-hexene dissolved in n-hexane was investigatedover sulfided Mo-Ni/Al2O3catalysts. The experimental results showed the catalysts have good cat-alytic performance for thioetherification reaction, but the isomerization and hydrogenation reactions of olefins over the catalysts can inhibit thioetherification reaction. As reaction temperature increases,the isomerization and hydrogenation reactions of olefins increase rapidly, however, the inhibition of thioetherification reaction also increases. The sulfur distribution and molecular structures of sulfurcompounds in the products were analyzed by the gas chromatograph with sulfur chemiluminescencedetector (GC-SCD) and the gas chromatograph/mass spectra spectrometry (GC/MS). Two possible routesof thioetherification reaction could be observed. At low temperature, the major pathway involves a directaddition of 1-butanethiol to the terminal carbon of double bond of 1-hexene. In this mechanism, the mainproduct is anti-Markovnikov adduct. At a higher temperature, the C S bond of 1-butanethiol can be sub-sequently cleaved, and the adsorbed -SH species can be formed on the catalysts. On the same time,abundant 1-hexene can be absorbed on the catalysts, as well. Therefore, the adsorbed SH species canthen recombine with adsorbed 1-hexene to form new hexyl-mercaptans, which can continue to produceanother kind of thioether (di-hexyl sulfide) with adsorbed 1-hexene. Similar with the first reaction route,the thioether of the anti-Markonikov adduct still dominates in the product.
Catalytic Hydrogenation of Thioesters, Thiocarbamates, and Thioamides
Luo, Jie,Rauch, Michael,Avram, Liat,Ben-David, Yehoshoa,Milstein, David
supporting information, p. 21628 - 21633 (2021/01/11)
Direct hydrogenation of thioesters with H2 provides a facile and waste-free method to access alcohols and thiols. However, no report of this reaction is documented, possibly because of the incompatibility of the generated thiol with typical hydrogenation catalysts. Here, we report an efficient and selective hydrogenation of thioesters. The reaction is catalyzed by an acridine-based ruthenium complex without additives. Various thioesters were fully hydrogenated to the corresponding alcohols and thiols with excellent tolerance for amide, ester, and carboxylic acid groups. Thiocarbamates and thioamides also undergo hydrogenation under similar conditions, substantially extending the application of hydrogenation of organosulfur compounds.
Characterization of initial reaction intermediates in heated model systems of glucose, glutathione, and aliphatic aldehydes
Wang, Tianze,Zhen, Dawei,Tan, Jia,Xie, Jianchun,Cheng, Jie,Zhao, Jian
, (2019/09/12)
To understand the effect of lipid degradation on Maillard formation of meaty flavors, initial reaction intermediates in model systems of glucose–glutathione with hexanal, (E)-2-heptenal, or (E,E)-2,4-decadienal were identified by HPLC–MS and by NMR. Besides Amadori compounds, hemiacetals and thiazolidines via addition of sulfhydryl to carbonyl or to the conjugated olefinic bond were found. Concentrations of all intermediates increased with reaction time while degradation of the intermediates with a glutathione moiety helped formation of thiazolidines with cysteinylglycine. The unsaturated aldehydes (E)-2-heptenal and (E,E)-2,4-decadienal exhibited high reactivity against glucose for glutathione, yielding higher levels of intermediate compounds than from glucose. Heating prepared intermediates reversibly released the original aldehydes, which caused various compounds formed by retro-aldol, oxidation, etc. to react with H2S and NH3. Among them, formation pathways including 3-nonen-2-one, 2-hexanoylfuran, and six dialkylthiophenes (e.g., 2-ethyl-5-(1-methylbutyl)thiophene) were proposed for the first time.
Phosphorus pentasulfide mediated conversion of organic thiocyanates to thiols
Maurya, Chandra Kant,Mazumder, Avik,Gupta, Pradeep Kumar
supporting information, p. 1184 - 1188 (2017/07/03)
In this paper we report an efficient and mild procedure for the conversion of organic thiocyanates to thiols in the presence of phosphorus pentasulfide (P2S5) in refluxing toluene. The method avoids the use of expensive and hazardous transition metals and harsh reducing agents, as required by reported methods, and provides an attractive alternative to the existing methods for the conversion of organic thiocyanates to thiols.
Two-step three-component process for one-pot synthesis of 8-alkylmercaptocaffeine derivatives
Rad, M. N. Soltani,Maghsoudi
, p. 70335 - 70342 (2016/08/06)
A highly efficient, odourless and two-step three-component process for one-pot synthesis of some 8-alkylmercaptocaffeine derivatives has been described. The catalyst-free three-component reaction of alkyl bromides, thiourea, and 8-bromocaffeine gave 8-alkylmercaptocaffeine products in excellent to quantitative yields. In addition, the impact of parameters on sample reaction is discussed.
A rhodium(i)-oxygen adduct as a selective catalyst for one-pot sequential alkyne dimerization-hydrothiolation tandem reactions
Kleinhans, George,Guisado-Barrios, Gregorio,Liles, David C.,Bertrand, Guy,Bezuidenhout, Daniela I.
supporting information, p. 3504 - 3507 (2016/03/04)
An air-stable rhodium(i)-oxygen adduct featuring a CNC-pincer ligand, based on 1,2,3-triazol-5-ylidenes, catalyzes the homo-dimerization and hydrothiolation of alkynes, affording the gem-enyne and α-vinyl sulfide isomers, respectively, with excellent selectivity. A one-pot stepwise strategy allows the selective catalytic preparation of non-symmetric bis-vinyl sulfides, as well as the alkyne dimerization-hydrothiolation tandem reactions.
A method of manufacturing a thiolcarboxylic compd.
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Paragraph 0026-0027, (2017/09/29)
PROBLEM TO BE SOLVED: To provide a method of production, obtaining a thiol compound in a high yield by using a hydroxy compound and hydrogen sulfide as raw materials. SOLUTION: This method of production includes reacting the hydroxy compound with hydrogen sulfide in the presence of a metal oxide catalyst selected from a complex metal oxide containing zirconia, acid-carrying zirconia or silica/titania having mesoporous pores, under gas phase heating, and it is especially useful for the production of an aromatic thiol compound such as thiophenol. COPYRIGHT: (C)2011,JPOandINPIT
Electromediators based on the Ni(II) and Cr(III) complexes with the redox-active ligands in the synthesis of sulfur-containing organic compounds
Okhlobystin,Smolyaninov,Okhlobystina,Berberova,Koldaeva, Yu. Yu.,Abdulaeva
, p. 33 - 36 (2013/02/23)
The chromium(III) tris-o-semiquinolate complex Cr(LSQ) 3 (LSQ is 3,6-di-tert-butyl-o-semiquinone) and the monoanionic paramagnetic nickel(II) complex [n-Bu4N][Ni(L S SQ)(L S DT)] (L S SQ is o-thiosemiquinone, L S DT is benzene-1,2-dithiolate) are considered as electromediators of hydrogen sulfide oxidation in the presence of various organic substrates (hex-1-ene, oct-1-ene, benzene, toluene, and benzoic acid). It is revealed that the electrolysis of hydrogen sulfide at the oxidation potential of the mediators in the presence of the substrates affords the corresponding aliphatic and aromatic thiols in a yield of 62-75%.
Synthesis and antifungal activities of alkyl N-(1,2,3-thiadiazole-4-carbonyl) carbamates and S-alkyl N-(1,2,3-thiadiazole-4-carbonyl) carbamothioates
Li, Zaifeng,Wu, Zengru,Luo, Fuying
, p. 3872 - 3876 (2007/10/03)
A series of alkyl N-(1,2,3-thiadiazole-4-carbonyl) carbamates and S-alkyl N-(1,2,3-thiadiazole-4-carbonyl) carbamothioates with unsubstituted or monobrominated straight chain alkyl groups were synthesized and evaluated as fungistatic agents against Gibberella zeae and Altemaria kikuchiana. These compounds showed variable antifungal activities at concentrations of 5 and 50 μg/mL The results showed that antifungal activities depended on the length of the alkyl chain with the optimal chain length of 6-11 carbons. Carbamic acid, (1,2,3-thiadiazole-4-ylcarbonyl)-, hexyl ester (4) showed a strong fungistatic activity against A. kikuchiana at both concentrations, with 90.7 and 54% growth inhibition at 50 and 5 μg/mL, respectively. Carbamic acid, (1,2,3-thiadiazole-4-ylcarbonyl)-, heptyl ester (5); Carbamic acid, (1,2,3-thiadiazole-4-ylcarbonyl)-, octyl ester (6); and Carbamic acid, (1,2,3-thiadiazole-4-ylcarbonyl)-, undecyl ester (9) showed strong fungistatic activity against G. zeae at both concentrations. Their growth inhibitions against G. zeae at the concentration of 5 μg/mL were 78, 63, and 59%, respectively.
