150-60-7Relevant articles and documents
NaI-Mediated Acetamidosulfenylation of Alkenes with Bunte Salts as Thiolating Reagent Leading to β-Acetamido Sulfides
Zhang, Rongxing,Yan, Zhaohua,Wang, Dingyi,Wang, Yuanxing,Lin, Sen
, p. 1195 - 1200 (2017)
A direct and efficient method for the acetamidosulfenylation reaction of alkenes was developed, in which NaI was used as a catalyst, DMSO as the oxidant, nitriles as both the solvent and nucleophiles and stable, readily available Bunte salts as thiolating reagents. The reactions were carried out under mild conditions generating β-acetamido sulfides in good yields. Moreover, the reaction can be performed when alcohols are used as nucleophiles providing the corresponding β-alkoxysulfides in moderate yields, respectively.
Direct preparation of anhydrous sodium oligosulfides from metal sodium and elemental sulfur in aprotic organic media directed toward synthesis of silane coupling agent
Yamada, Nobuo,Furukawa, Mutsuhisa,Nishi, Masayuki,Takata, Toshikazu
, p. 454 - 455 (2002)
Anhydrous sodium oligosulfide was prepared by the heterogeneous reaction of metal sodium and elemental sulfur in aprotic solvents. The oligosulfide consisted of a mixture of several Na2Sn (n = 2 - 8). Organic oligosulfides (R2Sn, n ≥ 2) including moisture-sensitive one were synthesized by the reaction with organic halides in high yeilds under mild conditions.
Reductive Dimerization of Organic Thiocyanates to Disulfides Mediated by Tetrathiomolybdate
Prabhu, Kandikere R.,Ramesha, A. R.,Chandrasekaran, Srinivasan
, p. 7142 - 7143 (1995)
An interesting reductive dimerization of organic thiocyanates assisted by benzyltriethylammonium tetrathiomolybdate, , 1, leads to the formation of the corresponding disulfides in high yields.
Sulfur transfer reactions of tetrathiomolybdate in water: Synthesis of alkyl disulfides from alkyl halides
Ilankumaran, Palanichamy,Prabhu, Kandikere R.,Chandrasekaran, Srinivasan
, p. 4031 - 4034 (1997)
Reaction of a number of alkyl halides with tetrathiomolybdate in water as the solvent affords the corresponding disulfides in good yields.
The oxidation of mercaptans by flavins.
Gibian,Winkelman
, p. 3901 - 3904 (1969)
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Kice,Morkved
, p. 2270,2271 (1964)
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Imidazole Promoted Highly Efficient Large-Scale Thiol-Free Synthesis of Symmetrical Disulfides in Aqueous Media
Mokhtari, Babak,Kiasat, Ali Reza,Monjezi, Javid
, p. 1573 - 1579 (2015)
A highly efficient and environmentally friendly method for the imidazole promoted preparation of symmetrical organic disulfides from Bunte salts is described. This thiol-free procedure produces the desired disulfides even on a large scale by reaction of Bunte salts with imidazole in good to high yields in aqueous media.
Kinetic investigation on liquid-liquid-solid phase transfer catalyzed synthesis of dibenzyl disulfide with H2S-laden monoethanolamine
Singh, Gaurav,Nakade, Priya G.,Mishra, Pratik,Jha, Preeti,Sen, Sujit,Mondal, Ujjal
, p. 78 - 86 (2016)
An investigation has been done on the utilization of H2S for the synthesis of dibenzyl disulfide (DBDS) using Amberlite IR-400 as a phase transfer catalyst. This involves absorption of H2S in aqueous monoethanolamine (MEA) followed by reaction of this H2S-laden MEA with organic reactant benzyl chloride (BC) to yield DBDS under liquid-liquid-solid (L-L-S) phase transfer catalysis condition. The effect of various parameters on the conversion of BC was studied and the selectivity of desired product was 100% at some level of process parameters. A suitable reaction mechanism has been proposed and a mathematical model has been developed to explain the kinetics of the reaction. Waste minimization was therefore affected with the utilization of H2S-laden gas for production of a value-added fine chemical.
Phthalimidomethyl Group. A New Protecting Group of Thiols
Gong, Young-Dae,Iwasawa, Nobuharu
, p. 2139 - 2142 (1994)
Phthalimidomethyl group is employed as a protecting group of thiols.This group can be introduced to thiols under mild reaction conditions and be removed by treatment with hydrazine hydrate followed by mercuric acetate or cupric acetate.
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Reich,H.J.,Jasperse,C.P.
, p. 5549 (1987)
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Reactivities of organic isothiocyanates and thiocyanates toward dialkyl bis(phosphine) complexes of palladium(II) and platinum(II)
Lee, Seon Gye,Choi, Keun-Young,Kim, Yong-Joo,Park, Sujin,Lee, Soon W.
, p. 880 - 887 (2015)
Room-temperature reactions of trans-[PdEt2L2] (L = PMe3, PEt3, PMe2Ph) with organic isothiocyanates [R-NCS; R = benzyl; CH(CH3)Ph, R-(-) and S-(+); indanyl, S-(+)] afforded the S,S-coordinated Pd(II) complexes [Pd(S2CN-R)L2] containing a dithiocarbonimidato (S2CN-R) group. Similar reactions involving allyl isothiocyanates produced the cationic η3-allyl Pd complex [Pd(η3-allyl)(PMe3)2]+(NCS)-. When [Pd(S2CN-R)(PMe3)2] was treated with 1 equiv of a chelating phosphine [L-L = depe (1,2-bis(diethylphosphino)ethane) and dmpe (1,2-bis(dimethylphosphino)ethane)], the corresponding complexes [Pd(S2CN-R)(L-L)] were produced. Reactions of trans-[PdEt2L2] (L = PMe3, PMe2Ph) with organic thiocyanates (R-SCN; R = benzyl, Et) resulted in the formation of [Pd(CN)2L2] and an organic disulfide by S-C bond cleavage of R-SCN. However, similar reactions of the dimethyl analogs, trans-[PdMe2L2] (L = PMe3, PEt3), with benzyl thiocyanate afforded different products, [Pd(NCS)2L2] or [PdMe(NCS)L2]. Treating [Pt(styrene)(PMe3)2] with benzyl isothiocyanate gave the S-coordinated dithiocarbonimidato Pt(II) complex, [Pt(S2CN-R)(Me3P)2] (R = benzyl). In contrast, cis-[PtEt2(PMe3)2] reacted with the isothiocyanate to afford the trialkyl Pt(IV) complex [PtEt2(SCN)(CH2Ph)(PMe3)2].
Fluorogenic hydrogen sulfide (H2S) donors based on sulfenyl thiocarbonates enable H2S tracking and quantification
Zhao, Yu,Cerda, Matthew M.,Pluth, Michael D.
, p. 1873 - 1878 (2019)
Hydrogen sulfide (H2S) is an important cellular signaling molecule that exhibits promising protective effects. Although a number of triggerable H2S donors have been developed, spatiotemporal feedback from H2S release in biological systems remains a key challenge in H2S donor development. Herein we report the synthesis, evaluation, and application of caged sulfenyl thiocarbonates as new fluorescent H2S donors. These molecules rely on thiol cleavage of sulfenyl thiocarbonates to release carbonyl sulfide (COS), which is quickly converted to H2S by carbonic anhydrase (CA). This approach is a new strategy in H2S release and does not release electrophilic byproducts common from COS-based H2S releasing motifs. Importantly, the release of COS/H2S is accompanied by the release of a fluorescent reporter, which enables the real-time tracking of H2S by fluorescence spectroscopy or microscopy. Dependent on the choice of fluorophore, either one or two equivalents of H2S can be released, thus allowing for the dynamic range of the fluorescent donors to be tuned. We demonstrate that the fluorescence response correlates directly with quantified H2S release and also demonstrate the live-cell compatibility of these donors. Furthermore, these fluorescent donors exhibit anti-inflammatory effects in RAW 264.7 cells, indicating their potential application as new H2S-releasing therapeutics. Taken together, sulfenyl thiocarbonates provide a new platform for H2S donation and readily enable fluorescent tracking of H2S delivery in complex environments.
Synthesis and reactivity of α-sulfenyl-β-chloroenones, including oxidation and Stille cross-coupling to form chalcone derivatives
Kearney, Aoife M.,Murphy, Linda,Murphy, Chloe C.,Eccles, Kevin S.,Lawrence, Simon E.,Collins, Stuart G.,Maguire, Anita R.
supporting information, (2021/05/04)
The synthesis of a range of novel α-sulfenyl-β-chloroenones from the corresponding α-sulfenylketones, via a NCS mediated chlorination cascade, is described. The scope of the reaction has been investigated and compounds bearing alkyl- and arylthio substituents have been synthesised. In most instances, the Z α-sulfenyl-β-chloroenones were formed as the major products, while variation of the substituent at the β-carbon position led to an alteration in stereoselectivity. Stille cross-coupling with the Z α-sulfenyl-β-chloroenones led to selective formation of Z sulfenyl chalcones, while the E α-sulfenyl-β-chloroenones did not react under the same conditions. Oxidation of the Z α-sulfenyl-β-chloroenones was followed by isomerisation, leading to the E α-sulfinyl-β-chloroenones. Stille cross-coupling with the E α-sulfinyl-β-chloroenones produced the E sulfinyl chalcones. Either the E or Z sulfinyl chalcones can be obtained by altering the sequence of oxidation and Stille cross-coupling.
Practical and efficient recyclable oxidative system for the preparation of symmetrical disulfides under aerobic conditions
Ling, Ong Chiu,Heidelberg, Thorsten,Ching, Juan Joon,Khaligh, Nader Ghaffari
, p. 281 - 294 (2020/12/13)
An efficient and practical oxidative coupling of thiols to symmetrical disulfides is developed at room temperature under aerobic conditions. The commercially available sodium methoxide solution 30 wt. % in methanol together with the air was used as a retrievable promoter system and green oxidant, respectively, for the preparation of symmetrical disulfides. The desired products were obtained in good to high yields by an economical procedure. No overoxidation of the symmetrical disulfides was observed, and various functional groups were well tolerated in the current protocol. Moreover, the new reagent reduces the generation of hazardous waste due to its high reusability. The reaction proceeded in the absence of light, and it was not inhibited by TEMPO. Also, the low yield of TEMPO-benzyl thiol adduct was detected under these conditions. Based on our experiments, a possible mechanism was proposed in the absence and presence of TEMPO.
Direct synthesis of sulfinic esters via ultrasound accelerated tandem reaction of thiols and alcohols with N-bromosuccinimide
Nguyen, Lan-Anh Thi,Le, Tri-Nghia,Duong, Cong-Thang,Vo, Chi-Tam,Duus, Fritz,Luu, Thi Xuan Thi
, p. 519 - 528 (2021/05/27)
The direct transformation of various thiols and simple alcohols with N-bromosuccinimide into sulfinic esters has been investigated by using different categories of base/acidic catalysts as well as co-solvents under varied reaction conditions. The reaction was found out to afford the sulfinic esters with high yields in the absence of catalysts, especially within the shorter time under the acceleration of ultrasonic irradiation than under the longer-lasting conventional stirring conditions.
