The synthesis of symmetrical disulfides by reacting organic halides with Na₂S₂O₃·5H₂O in DMSO

Abstract

Symmetrical disulfides were prepared by heating organic halides with Na2S2O3 in DMSO in high yields and good purities.

Tethered Blatter Radical for Molecular Grafting: Synthesis of 6-Hydroxyhexyloxy, Hydroxymethyl, and Bis(hydroxymethyl) Derivatives and Their Functionalization

“…Disulfides Id and IId were obtained in 18% yield from tosylates Ib and IIb using a general procedure [65] involving reactions with the thiosulfate (S 2 O 3 2− ) nucleophile in DMSO, followed by oxidation of the resulting mercaptan with I 2 (Scheme 4). In contrast, the preparation of azide Ie was straightforward and more efficient.…”

“…ether/AcOEt 4:1) and further by recrystallization (CH 2 Cl 2 /EtOH) to give 967 mg (40% yield) of triazine 2 as yellow crystals: mp 136-137 • C; 1 H NMR (500 MHz, CDCl 3 ) 8.84 (s, 1H), 8.76 (d, J = 8.3 Hz, 2H), 8.21 (d, J = 8.9 Hz, 1H), 8.11 (dd, J 1 = 8.9 Hz, J 2 = 1.9 Hz, 1H), 7.58 (d, J = 8.4 Hz, 2H), 5.23 (s, 2H), 2.16 (s, 3H). 13 C{ 1 H} NMR (151 MHz, CDCl 3 ) δ 170.9, 160.6, 145.3, 142.1, 140.4, 134.8, 132.0 (q, J = 34 Hz), 131.1 (q, J = 3 Hz), 131.0, 129.5, 128.7, 128.0 (q, J = 4 Hz), 123.2 (q, J = 273 Hz), 65…”

Selective synthesis of α-organylthio esters and α-organylthio ketones from β-keto esters and sodiumS-organyl sulfurothioates under basic conditions

“…Therefore, they have been actively studied as precursors for the preparation of diverse sulfur-containing compounds [1]. These recent findings include their use in direct sulfenylation reactions of electron-rich N-heterocycles [2][3][4], decarboxylative cross-coupling reactions with propiolic acid derivatives [5], Michael addition reaction [6], cross-couplings catalyzed by Pd [7] and Cu salts [8,9], the preparation of symmetrical and nonsymmetrical disulfides [10,11], and the synthesis of β-acetamido sulfides by the acetamidosulfenylation of alkenes [12], among others [13][14][15].…”

NaI-Mediated Acetamidosulfenylation of Alkenes with Bunte Salts as Thiolating Reagent Leading to β-Acetamido Sulfides

“…On the basis of the reported literatures 8,[11][12][13][14] and the above results of control experiments, a plausible mechanism is depicted in Scheme 7. Under the heating conditions, the hydrolysis of Bunte salts A in the presence of water leads to the formation of species bisulfate anion and thiol or thiol anion B in the reaction mixture.…”

“…Under the heating conditions, the hydrolysis of Bunte salts A in the presence of water leads to the formation of species bisulfate anion and thiol or thiol anion B in the reaction mixture. 11 The disulfide C are thus generated through the attack by thiol or thiol anion B on another Bunte salt A. 12 Next, the reaction of disulfide C with I 2 to gives RSI D which is an electrophilic species, 13a and an intermediate F appeared via the attack of alkene E by RSI D. 8a,13b The subsequent reaction of the intermediate F with nitriles followed by Ritter reaction, alcohol affords β-acetamido sulfides G, and β-alkoxy sulfides I with the release of HI.…”