25769-92-0Relevant articles and documents
From symmetrical tetrasulfides to trisulfide dioxides: Via photocatalysis
Gong, Kai,Jiang, Xuefeng,Zhou, Yilin
supporting information, p. 9865 - 9869 (2021/12/24)
A straightforward strategy involving photocatalysis has been established for accessing trisulfide dioxides from readily achieved symmetrical tetrasulfides. Stern-Volmer analysis and radical quenching experiments demonstrated the occurrence of a single electron transfer between the photocatalyst and sulfinic acid. Bioactive molecules such as the antihypertensive drug captopril, allicin derivatives, amino acids and terpenes were efficiently and reversibly linked through sulfur-sulfur covalent bonds. Furthermore, flow-setup syntheses of trisulfide dioxides were successfully achieved on the gram scale, indicating the great potential of the developed protocol for practical industrial applications. This journal is
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.
Applications of Synthetic Organic Tetrasulfides as H2S Donors
Cerda, Matthew M.,Hammers, Matthew D.,Earp, Mary S.,Zakharov, Lev N.,Pluth, Michael D.
supporting information, p. 2314 - 2317 (2017/05/12)
In an effort to expand the availability of simple polysulfides for H2S donation, we report here the synthesis and H2S release profiles of bis(aryl) and bis(alkyl) tetrasulfides. The tetrasulfide donors release H2S in a first-order dependence on reduced glutathione (GSH) and release more H2S than the commonly used trisulfide DATS.
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
Insertion of a two sulfur unit into the S-S bond - Tailor-made polysulfides
Rys,Harpp
, p. 7169 - 7172 (2007/10/03)
Triphenylthiosulfenyl chloride (1) reacts with disulfides RSSR, yielding tetrasulfides as the main products. The results of the insertion for different R groups are reported. A two-step mechanism involving the formation of unsymmetrical trisulfide intermediates containing the trityl group is proposed. (C) 2000 Elsevier Science Ltd.
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,.
Reactions of Triphenylphosphine with Di-, Tri-, or Tetrasulphides, or with Sulphur, in Hydroxylic Solvents.
Demarcq, Michel C.
, p. 3052 - 3080 (2007/10/02)
In contrast to the behaviour of disulphides RS2R, the mono-desulphurisation of tri- or tetra-sulphides RSnR (R = benzyl, p-tolyl; n= 3, 4) by triphenylphosphine in hydroxylic solvents (methanol-benzene or water- 2-propanol-benzene) mainly affords Ph3PS with only small (n = 3) or very small (n = 4) amounts of Ph3PO.Ph3PO was virtually absent in the reaction products of Ph3P with 2Sn (n = 2, 3) or with elemental sulphur in alcoholic or aqueous media.Reaction rates for the formation of Ph3PS or Ph3PO decrease in the order: RS4R > RS3R >> RS2R (R = benzyl or p-tolyl) and hydroxylic >> aprotic solvents; the dependence on R is: (EtO)2P(S) >> p-tolyl > benzyl.Addition of a thiol impedes the formation of Ph3PO; low pH's have an opposite effect.The results are rationalised in terms of basicity of anions RSp- (p = 1 to n-1), relative softness of terminal or central S in RSnR and Broensted acidity of the solvent.An alternative is proposed to the Bartlett's mechanism for the reaction of S8 with Ph3P, in which the intermediate zwitterion Ph3P+S4- collapses by fast intramolecular nucleophilic displacement, affording Ph3PS and highly reactive S7.
