4991-51-9Relevant academic research and scientific papers
Accelerated reduction and solubilization of elemental sulfur by 1,2-aminothiols
Stoffel, Jonathan T.,Riordan, Kimberly T.,Tsui, Emily Y.
supporting information, p. 12488 - 12491 (2021/12/04)
Nucleophilic 1,2-aminothiol compounds readily reduce typically-insoluble elemental sulfur to polysulfides in both water and nonpolar organic solvents. The resulting anionic polysulfide species are stabilized through hydrogen-bonding interactions with the proximal amine moieties. These interactions can facilitate sulfur transfer to alkenes.
3,4-Dichloro-1,2,5-thiadiazole: a commercially available electrophilic sulfur transfer agent and safe resource of ethanedinitrile
Gorjian, Hayedeh,Khaligh, Nader Ghaffari
, (2021/11/04)
3,4-Dichloro-1,2,5-thiadiazole is introduced as a safe and efficient sulfur transfer reagent. By applying this commercially available reagent, the symmetrical trisulfides and ethanedinitrile were simultaneously obtained by reacting various thiols with this reagent at room temperature. This reagent is non-toxic, inexpensive, and commercially available. In addition, no higher-order polysulfides were detected in all cases after the completion of the reaction. The short reaction times (20–50 min), excellent selectivity, and high yield of the trisulfides are some attractive merits of this reagent for the preparation of trisulfides. The reaction is one-pot, and isolation-purification of intermediates is not required. The procedure was readily scaled up to 5 grams. A mechanism is presented to explain the chemistry.
Electrochemical Synthesis of Organic Polysulfides from Disulfides by Sulfur Insertion from S8 and an Unexpected Solvent Effect on the Product Distribution
F?hrmann, Jan,Hilt, Gerhard
, p. 11141 - 11149 (2021/06/09)
An electrochemical synthesis of organic polysulfides through sulfur insertion from elemental sulfur to disulfides or thiols is introduced. The highly economic, low-sensitive and low-priced reaction gives a mixture of polysulfides, whose distribution can be influenced by the addition of different amounts of carbon disulfide as co-solvent. To describe the variable distribution function of the polysulfides, a novel parameter, the “absorbance average sulfur amount in polysulfides” (SAP) was introduced and defined on the basis of the “number average molar mass” used in polymer chemistry. Various organic polysulfides were synthesized with variable volume fractions of carbon disulfide, and the yield of each polysulfide was determined by quantitative 13C NMR. Moreover, by using two symmetrical disulfides or a disulfide and a thiol as starting materials, a mixture of symmetrical and asymmetrical polysulfides could be obtained.
TBAF promoted formation of symmetrical trisulfides
Lach, Slawomir,Witt, Dariusz
, p. 10 - 14 (2014/02/14)
We have developed a new method for the synthesis of functionalized symmetrical trisulfides based on (5,5-dimethyl-2-thioxo-1,3,2-dioxa-phosphorin- 2-yl)disulfanyl derivatives prepared from readily available 5,5-dimethyl-2-sul- fanyl-2-thioxo-1,3,2-dioxaph
Novel and efficient methods for the synthesis of symmetrical trisulfides
Kertmen, Ahmet,Lach, Slawomir,Rachon, Janusz,Witt, Dariusz
experimental part, p. 1459 - 1462 (2009/12/08)
We have developed convenient methods for the synthesis of symmetrical trisulfides under mild conditions in very good yields. The described methods are based on the straightforward preparation of (5,5-dimethyl-2-thioxo-1,3,2- dioxaphosphorin-2-yl)disulfany
Rhodium-catalyzed sulfur atom exchange reaction between organic polysulfides and sulfur
Arisawa, Mieko,Tanaka, Ken,Yamaguchi, Masahiko
, p. 4797 - 4800 (2007/10/03)
RhH(PPh3)4 and cis-1,2-bis(diphenylphosphino)ethylene (dppv) catalyze the exchange of sulfur atoms between sulfur and organic polysulfides. The exchange of dialkyl trisulfides with sulfur proceeds at a high efficiency within 5 min at room temperature yielding a mixture of organic polysulfides.
Optimization of the synthesis of symmetric aromatic tri- and tetrasulfides
Zysman-Colman, Eli,Harpp, David N.
, p. 2487 - 2489 (2007/10/03)
The reaction of aromatic thiols with sulfur dichloride and sulfur monochloride to form the corresponding aromatic trisulfides, 2a-d, and tetrasulfides, 3a-d, has been optimized with respect to yield and purity. The use of pyridine as an amine base and the
Kaolinitic clay catalyzed reaction of sulfur monochloride with aromatics: An efficient and high yield synthesis of symmetrical disulfides
Vyas, Renu,Chanda, Bhanu,Sudalai
, p. 43 - 44 (2007/10/03)
Kaolinitic clay efficiently catalyses the reaction of sulfur monochloride with arenes to yield symmetrical 4,4′ arene disulfides in a single step under heterogeneous phase.
Use of a sacriflcial-sulfur electrode in electroorganic chemistry. V. Formation of the sequence CSSSC from S and thiols or thiolates
Do, Quang Tho,Elothmani, Driss,Simonet, Jacques,Guillanton, Georges Le
, p. 273 - 281 (2007/10/03)
At a working potential of about +2.0 V (vs SCE) the carbon-sulfur electrode is a source of the electrogenerated cation S2+. In organic media, this electrophile reacts with thiols (or thiolates) to give a mixture of polysulfides of which the trisulfide is the main product. The reaction between electrogenerated Sy2- and alkyl halides is less selective. Elsevier,.
Displacement of aromatic nitro groups by anionic sulfur nucleophiles: reactivity of aryl disulfide and thiolate ions towards dinitrobenzenes in N,N-dimethylacetamide
Robert, Julie,Anouti, Meriem,Bosser, Gerard,Parrain, Jean-Luc,Paris, Jacky
, p. 1639 - 1644 (2007/10/02)
Nucleophilic substitutions of 1,2- and 1,4-dinitrobenzenes (oDNB and pDNB) by thiolates ArS- (a) and aryl disulfide ions ArS2- (b) have been studied in dilute solutions by spectroelectrochemistry in N,N-dimethylacetamide.Compounds 1b-2b are the predominant reactive species in ArSx- (x=2) solutions when sulfur is added to electrogenerated thiolates 1a-2a.In all cases the addition of dinitrobenzenes led to the fast displacement of one of the NO2 groups at room temperature.With thiolate ions, the stoichiometric formation of the expected unsymmetrical diaryl monosulfides NO2C6H4SAr was observed.Aryl disulfide ions reacted in two successive steps: (i) SNAr substitution affording NO2C6H4S2Ar; (ii) displacement of NO2C6H4Sx- ions (x=1,2) by S-nucleophilic attack of the S-S bond or a concurrent redox process.Reactions between 4-CH3C6H4Sx- (x=2) ions and oDNB or pDNB which were performed on the preparative scale confirmed the formation of mixtures of Ar2S2 and Ar2S3 symmetrical polysulfides.
