10496-15-8Relevant articles and documents
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Liu,Tong
, p. 669 (1978)
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The Reaction of Electron-deficient Selenoaldehydes with Thiols
Duchenet, Virginie,Vallee, Yannick
, p. 4925 - 4926 (1993)
Electron-poor selenoaldehydes, generated in-situ in refluxing toluene, reacted with thiols in the presence of triethylamine to give selenenyl sulfides, RSeSR'.The formation of a selenodisulfide, RSSeSR, was also evidenced.
Facile solvent-free generation of disulfide dianion and its use for preparation of symmetrical disulfides
Kiasat, Ali Reza,Mokhtari, Babak,Savari, Ali,Kazemi, Foad
, p. 178 - 182 (2008)
A variety of symmetrical dialkyl disulfides were prepared from the reaction of alkyl halides, sodium hydroxide and elemental sulfur under solvent free conditions. The reaction proceeded very fast and produced the desired products in moderate to excellent isolated yields.
Selective, cofactor-mediated catalytic oxidation of alkanethiols in a self-assembled cage host
Da Camara, Bryce,Dietz, Philip C.,Chalek, Kevin R.,Mueller, Leonard J.,Hooley, Richard J.
, p. 14263 - 14266 (2020)
A spacious Fe(ii)-iminopyridine self-assembled cage complex can catalyze the oxidative dimerization of alkanethiols, with air as stoichiometric oxidant. The reaction is aided by selective molecular recognition of the reactants, and the active catalyst is derived from the Fe(ii) centers that provide the structural vertices of the host. The host is even capable of size-selective oxidation and can discriminate between alkanethiols of identical reactivity, based solely on size. This journal is
Water accelerated Sm/TMSCl reductive system: Debromination of vic- dibromides and reduction of sodium alkyl thiosulfates
Xu, Xiaoliang,Lu, Ping,Zhang, Yongmin
, p. 1917 - 1925 (2000)
A simple and efficient method for the debromination of vic-dibromides to (E)-alkenes and reduction of sodium alkyl thiosulfates to disulfides promoted by Sm/TMSCl/H2O (trace) has been described.
Preparation, structures, and physical properties of tetrakis(alkylthio) tetraselenafulvalene (TTCn-TSeF, n = 1-15)
Saito, Gunzi,Yoshida, Yukihiro,Murofushi, Hidenobu,Iwasawa, Naoko,Hiramatsu, Takaaki,Otsuka, Akihiro,Yamochi, Hideki,Isa, Kimio,Mineo-Ota, Eriko,Konno, Michiko,Mori, Takehiko,Imaeda, Ken-Ichi,Inokuchi, Hiroo
, p. 335 - 344 (2010)
A series of tetrakis(alkylthio)tetraselenafulvalene compounds (TTC n-TSeF, n = 1-15) were prepared by a one-step reaction between dialkyl disulfide and tetralithiated TSeF. Molecular properties (redox potentials and optical absorptions in solution) and solid-state properties (thermal behaviors, electric conductivities, and molecular and crystal structures for n = 1 and 10) were studied. TTCn-TSeF compounds are weak electron donor molecules and characterized by small on-site Coulomb repulsion. TTC1-TSeF has a high-dimensional conduction network owing to the presence of highdimensional heteroatomic contacts, "Atomic-Wire Effect." The π-moieties of TTC10-TSeF were fastened by the alkyl chains ("Fastener Effect") to form π-columns and there are a variety of short heteroatomic contacts resulting in two dimensional electronic structure. Electrical conductivity exhibited peculiar enhancement for n = 1 and 7 ≤ n ≤ 14 owing to the presence of high-dimensional conduction paths. These compounds may manifest high carrier mobility, and are good candidates for the field-effect transistor channel based on the advantageous features: low dark conductivity, low donor ability, on-site Coulomb repulsion energy, high-dimensional π-electron structure, and high solubility in organic solvents.
Aerobic Oxidation of Thiols Catalyzed by Copper Nanoparticles Supported on Diamond Nanoparticles
Dhakshinamoorthy, Amarajothi,Navalon, Sergio,Sempere, David,Alvaro, Mercedes,Garcia, Hermenegildo
, p. 241 - 246 (2013)
After purification by Fenton treatment, commercial diamond nanoparticles (NPs) are a suitable solid support for the deposition of Cu nanoparticles. Heating at 500°C under hydrogen proved to be a convenient annealing process for Fenton-purified diamond NPs that decreased the population of surface carboxylic acid groups and lead to samples with average Cu particle sizes of 3-4nm. The samples of Cu NPs supported on diamond NPs have been characterized by IR and X-ray photoelectron spectroscopy, as well as XRD and TEM. It was concluded that the samples contained Cu0 as well as CuI and CuII species. The resulting diamond-supported Cu NPs were highly active for the selective aerobic oxidation of aromatic thiols to the corresponding disulfides, whereas aliphatic thiols exhibited much lower reactivity because of some poisoning and catalyst deactivation produced by aliphatic thiols. The Cu catalysts used for thiophenol oxidation could be reused in four consecutive runs with 4% of decrease in the catalytic activity. This Cu catalyst exhibited similar catalytic activity, but is considerably more affordable, as an analogous diamond-supported Au catalyst.
Preparation of disulfides by the oxidation of thiols using bromine
Wu, Xiaoming,Rieke, Reuben D.,Zhu, Lishan
, p. 191 - 196 (1996)
Medium length aliphatic disulfides are easily synthesized via the bromine-oxidation of thiols in the absence of solvent. Bromine can also oxidize long aliphatic and aromatic thiols to disulfides in solution. All yields are quantitative.
Nitrosonium-catalyzed decomposition of S-nitrosothiols in solution: A theoretical and experimental study
Zhao, Yi-Lei,McCarren, Patrick R.,Houk,Choi, Bo Yoon,Toone, Eric J.
, p. 10917 - 10924 (2005)
The decomposition of S-nitrosothiols (RSNO) in solution under oxidative conditions is significantly faster than can be accounted for by homolysis of the S-N bond. Here we propose a cationic chain mechanism in which nitrosation of nitrosothiol produces a nitrosated cation that, in turn, reacts with a second nitrosothiol to produce nitrosated disulfide and the NO dimer. The nitrosated disulfide acts as a source of nitrosonium for nitrosothiol nitrosation, completing the catalytic cycle. The mechanism accounts for several unexplained facets of nitrosothiol chemistry in solution, including the observation that the decomposition of an RSNO is accelerated by O2, mixtures of O 2 and NO, and other oxidants, that decomposition is inhibited by thiols and other antioxidants, that decomposition is dependent on sulfur substitution, and that decomposition often shows nonintegral kinetic orders.
Aerobic oxidation of thiols to disulfides using iron metal-organic frameworks as solid redox catalysts
Dhakshinamoorthy, Amarajothi,Alvaro, Mercedes,Garcia, Hermenegildo
, p. 6476 - 6478 (2010)
Aerobic oxidation of thiols to disulfides has been carried out using iron metal-organic frameworks (MOFs) as solid redox catalysts with very high yield and selectivity in acetonitrile under mild reaction conditions.
Reductive cleavage of S-S bond by samarium diiodide: A novel method for the synthesis of disulfides
Jia,Zhang,Zhou
, p. 2893 - 2898 (1994)
Samarium diiodide reductively cleaves the S-S bond of sodium alkyl thiosulfates to give the corresponding disulfides in moderate to good yields under mild and neutral conditions.
Electrochemical synthesis of organochalcogenides in aqueous medium
Ribeiro Neto, Pedro B.,Santana, Sonydelane O.,Levitre, Guillaume,Galdino, Danilo,Oliveira, Jadson L.,Ribeiro, Rogério T.,Barros, Maria E. S. B.,Bieber, Lothar W.,Menezes, Paulo H.,Navarro, Marcelo
, p. 657 - 661 (2016)
The electrochemical preparation of telluride, selenide and sulfide ions was carried out in NaOH aqueous solution, using a two compartment cell. Organochalcogenides were prepared from halogenated compounds in a two-step procedure. The monochalcogenides were obtained as the major products in good yields.
Boron nitride nanoplatelets as a solid radical initiator for the aerobic oxidation of thiophenol to diphenyldisulfide
Dhakshinamoorthy, Amarajothi,Primo, Ana,Esteve-Adell, Ivan,Alvaro, Mercedes,Garcia, Hermenegildo
, p. 776 - 780 (2015)
Boron nitride (BN) nanoplatelets suspended in ethanol were obtained through the sonication of BN powders prepared through biopolymer-templated pyrolysis and air calcination of (NH4)3BO3-chitosan powders. AFM measurements indicate that BN nanoplatelets have an average height of 1.5 nm and length and width dimensions between 30 and 100 nm. BN nanoplatelets exhibit higher catalytic activity for the molecular oxygen-mediated oxidation of aromatic thiols to the corresponding disulfides than do boron and nitrogen-codoped graphene or commercial bulk hexagonal BN. The reaction scope includes substituted aromatic and heteroaromatic thiols, whereas aliphatic thiols are considerably less reactive. The hot filtration test and radical quenching by N-tert-butyl-α-phenylnitrone support an autoxidation mechanism involving thiyl radicals. BN nanoplatelets are deactivated during the course of the reaction owing to aggregation. The present study uncovers the activity of BN nanoplatelets used as an insoluble radical initiator of S-H bonds. Aerobics is fun: Boron nitride nanoplatelets prepared through pyrolysis and sonication demonstrate higher catalytic activity for the aerobic oxidation of thiophenol.
Reactions of chlorine dioxide with organic compounds 2. Oxidation of thiols
Lezna,Rubtsova,Kuchin
, p. 1877 - 1878 (2003)
Oxidation of thiols with chlorine dioxide smoothly affords the corresponding disulfides.
Synthesis of Disulfides by Copper-Catalyzed Disproportionation of Thiols
Choi, Jaesung,Yoon, Nung Min
, p. 3266 - 3267 (1995)
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A new reagent for the efficient synthesis of disulfides from alkyl halides
Polshettiwar, Vivek,Nivsarkar, Manisha,Acharya, Jyotiranjan,Kaushik
, p. 887 - 889 (2003)
Benzyltriethylammonium tetracosathioheptamolybdate [(C6H5CH2N(Et)3)6Mo 7S24] has been found to be a superior sulfur transfer reagent for the conversion of alkyl halides to the corresponding disulfides in excellent yields under very mild reaction conditions.
Application of Bulky NHC-Rhodium Complexes in Efficient S-Si and S-S Bond Forming Reactions
Bo?t, Ma?gorzata,?ak, Patrycja
supporting information, p. 17579 - 17585 (2021/11/18)
The efficient and straightforward syntheses of silylthioethers and disulfides are presented. The synthetic methodologies are based on new rhodium complexes containing bulky N-heterocyclic carbene (NHC) ligands that turned out to be efficient catalysts in thiol and thiol-silane coupling reactions. These green protocols, which use easily accessible reagents, allow obtaining compounds containing S-Si and S-S bonds in solvent-free conditions. Additionally, preliminary tests on coupling of mono- and octahydro-substituted spherosilicates with selected thiols have proved to be very promising and showed that these catalytic systems can be used for the synthesis of a novel class of functionalized silsesquioxane derivatives.
Natural gallic acid catalyzed aerobic oxidative coupling with the assistance of MnCO3 for synthesis of disulfanes in water
Song, Lijuan,Li, Wenhao,Duan, Wenxue,An, Jichao,Tang, Shanyu,Li, Longjia,Yang, Guanyu
supporting information, p. 1432 - 1438 (2019/03/26)
The formation of S-S bonds has great significance and value in synthetic chemistry and bioscience. To pursue a sustainable approach for such a synthesis, an aerobic oxidative coupling method for the efficient preparation of organic disulfanes, using a low-toxic natural gallic acid as an organocatalyst, inexpensive MnCO3 as a cocatalyst, O2 as the terminal oxidant and water as the solvent, has been successfully developed. Such metal-organic cooperative catalytic protocol provided an access to various symmetrical and unsymmetrical disulfanes in up to 99% yield. Gram scale synthesis with practical convenience and low loading of catalysts further illustrates the practicability of our method.
