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.
Synthesis and characterization of benzylidene bis-dithiobenzoate
Quintanilla, Ma. Gloria,Guerra, Eva,Dotor, Jessica,Maresova, Jirina,Barba, Fructuoso,Martin, Avelino
, p. 1691 - 1699 (2005)
Benzal chloride reacts with sodium sulfide in alcoholic solution to yield three main products: benzyl disulfide, benzyl dithiobenzoate, and a new interesting compound 5, C21H16S4, which was isolated and characterized as benzylidene bis-dithiobenzoate. The intermediates obtained from the autoxidation-reduction of the unisolable thiobenzaldehyde are implied in subsequent nucleophilic addition and substitution processes. NMR spectra and X-Ray structure analysis of 5 are discussed. Copyright Taylor & Francis Inc.
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.
A convenient method for production of thionitrites and disulfides under mild and heterogeneous condition
Zolfigol, Mohammad Ali
, p. 1593 - 1597 (2000)
Thiols can be readily converted to their corresponding thionitrite with a combination of inorganic acidic salts and sodium nitrite in dichloromethane at room temperature. Disulfides result from the homolytic cleavage of the sulfur-nitrogen bond of the unstable thionitrite and subsequent coupling of the resultant thiyl radicals.
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.
Convenient stereoselective synthesis of 3-hydroxy-2-iodo-2(E)-alkenyl sulfides via iodohydroxylation of 1,2-allenyl sulfoxides in the presence of BnSH
Fu, Chunling,Huang, Xian,Ma, Shengming
, p. 6063 - 6065 (2004)
The iodohydroxylation of 1,2-allenyl sulfoxides with I2 in the presence of BnSH affords 3-hydroxy-2-iodo-2(E)-alkenyl sulfides in good yields and selectivities. The stereochemistry for the products of this transformation is opposite to what was obtained from the iodohydroxylation of 1,2-allenyl sulfides. Based on the results of some control experiment, a mechanism was proposed.
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.
Copper(I)/S8 reversible reactions leading to an end-on bound dicopper(II) disulfide complex: Nucleophilic reactivity and analogies to copper-dioxygen chemistry
Maiti, Debabrata,Woertink, Julia S.,Vance, Michael A.,Milligan, Ashley E.,Narducci Sarjeant, Amy A.,Solomon, Edward I.,Karlin, Kenneth D.
, p. 8882 - 8892 (2007)
Elemental sulfur (S8) reacts reversibly with the copper(I) complex [(TMPA′)CuI]+ (1), where TMPA′ is a TMPA (tris(2-pyridylmethyl)amine) analogue with a 6-CH2OCH 3 substituent on one pyridyl ligand arm, affording a spectroscopically pure end-on bound disulfido-dicopper(II) complex [{(TMPA′)CuII}2(μ-1,2-S2 2-)]2+ (2) {ν(S-S) = 492 cm-1; ν(Cu-S)sym = 309 cm-1}; by contrast, [(TMPA)Cu I(CH3CN)]+ (3)/S8 chemistry produces an equilibrium mixture of at least three complexes. The reaction of excess PPh3 with 2 leads to formal "release" of zerovalent sulfur and reduction of copper ion to give the corresponding complex [(TMPA′)-CuI(PPh3)]+ (11) along with S=PPh3 as products. Dioxygen displaces the disulfur moiety from 2 to produce the end-on Cu2O2 complex, [{(TMPA′)Cu II}2(μ-1,2-O22-)]2+ (9). Addition of the tetradentate ligand TMPA to 2 generates the apparently more thermodynamically stable [{(TMPA)CuII}2(μ-1,2-S 22-)]2+ (4) and expected mixture of other species. Bubbling 2 with CO leads to the formation of the carbonyl adduct [(TMPA′)CuI-(CO)]+ (8). Carbonylation/sulfur- release/CO-removal cycles can be repeated several times. Sulfur atom transfer from 2 also occurs in a near quantitative manner when it is treated with 2,6-dimethylphenyl isocyanide (ArNC), leading to the corresponding isothiocyanate (ArNCS) and [(TMPA′)CuI(CNAr)]+ (12). Complex 2 readily reacts with PhCH2Br: [{(TMPA′)Cu II}2(μ-1,2-S22-)]2+ (2) + 2 PhCH2Br → [{(TMPA′)-CuII(Br)} 2]2+ (6) + PhCH2SSCH2Ph. The unprecedented substrate reactivity studies reveal that end-on bound μ-1,2-disulfide-dicopper(II) complex 2 provides a nucleophilic S 22- moiety, in striking contrast to the electrophilic behavior of a recently described side-on bound μ-η2: η2-disulfido-dicopper(II) complex, [{(N3)Cu II}2(μ-η2:η2-S 22-)]2+ (5) with tridentate N3 ligand. The investigation thus reveals striking analogies of copper/sulfur and copper/dioxygen chemistries, with regard to structure type formation and specific substrate reactivity patterns.
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.
