4235-78-3Relevant academic research and scientific papers
Fenton-Inspired C-H Functionalization: Peroxide-Directed C-H Thioetherification
Groendyke, Brian J.,Modak, Atanu,Cook, Silas P.
, p. 13073 - 13091 (2019/10/10)
Substoichiometric iron mediates the thioetherification of unactivated aliphatic C-H bonds directed by resident silylperoxides. Upon exposure to a catalytic amount of iron(II) triflate, TIPS-protected peroxides bearing primary, secondary, and tertiary C-H sites undergo chemoselective thioetherification of remote C-H bonds with diaryl disulfides. The reaction demonstrates a broad substrate scope and functional group tolerance without the use of any noble metal additives. Mechanistic experiments suggest that the reaction proceeds through 1,5-H atom abstraction by a hydroxyl radical generated with iron.
Chemoselective synthesis of diaryl disulfides via a visible light-mediated coupling of arenediazonium tetrafluoroborates and CS2
Leng, Jing,Wang, Shi-Meng,Qin, Hua-Li
supporting information, p. 903 - 909 (2017/06/23)
A highly efficient and chemoselective method for the synthesis of diaryl disulfides is developed via a visible light-promoted coupling of readily accessible arenediazonium tetrafluoroborates and CS2. This practical and convenient protocol provides a direct pathway for the assembly of a series of disulfides in an environmentally friendly manner with good to excellent yields.
Decarboxylative Giese-Type Reaction of Carboxylic Acids Promoted by Visible Light: A Sustainable and Photoredox-Neutral Protocol
Ramirez, Nieves P.,Gonzalez-Gomez, Jose C.
supporting information, p. 2154 - 2163 (2017/04/24)
We describe herein a transition-metal-free method for the decarboxylative generation of radicals from carboxylic acids and their 1,4-addition to Michael acceptors. The Fukuzumi catalyst (9-mesitylene-10-methylacridinium perchlorate, [Acr-Mes]ClO4) enabled this transformation under visible-light irradiation at room temperature with CO2 as the only byproduct. The scope and limitations of this protocol were examined by using a range of Michael acceptors (15 examples) and carboxylic acids (18 examples). The use of 3-hydroxypivalic acid in this protocol allowed the straightforward formation of a diastereomerically pure δ-lactone. Moreover, when a homoallylic acid was used, a radical cascade reaction took place with the formation of three C–C bonds.
An improved method for the synthesis of disulfides by periodic acid and sodium hydrogen sulfite in water
Khan, Khalid M.,Taha, Muhammad,Rahim, Fazal,Ali, Muhammad,Jamil, Waqas,Perveen, Shahnaz,Iqbal Choudhary
experimental part, p. 415 - 419 (2011/03/22)
An improved method for the synthesis of disulfide in water by using periodic acid and sodium hydrogen sulfite was developed.
Synthesis of aryl perfluoroalkyl sulfides from aromatic disulfides
Sipyagin,Enshov,Kashtanov,Potemkin,Thrasher,Waterfeld
, p. 420 - 434 (2007/10/03)
Thermolysis of xenon(II) bis(perfluoroalkanecarboxylates) in the presence of diaryl disulfides occurs through the S-S bond cleavage to form dihalo-, halonitro-, and halodinitrophenyl perfluoroalkyl sulfides. The latter type of compounds was obtained for the first time. The main side process is the perfluoroalkylation of the aromatic ring.
Organic Disulfides and Related Substances. 45. Synthesis and Properties of Some Disulfide Sulfinate Salts Containing No Nitrogen
Srivastava, Pramod K.,Field, Lamar
, p. 252 - 254 (2007/10/02)
Disulfide sulfinates of the structure RSS(CH2)4SO2Na were synthesized by reaction of 1,2-dithiane 1,1-dioxide (1), thiols, and sodium methoxide in methanol.Disproportionation was minimized by precipitating and reprecipitating the products with ether as quickly as possible; where R = aryl, protection from light is advisable.The groups R typify large lipophilic ones (n-decyl, 1-adamantyl), small hydrophilic ones (2-carboxyethyl, 2,3-dihydroxypropyl), disulfide sulfinates , and aryl groups substituted by electron-donating or electron-withdrawing groups.The products usually were quite hygroscopic and were isolated as hydrates.They disproportionated with varying ease in aqueous solution either to 1 or to the two symmetrical disulfides, RSSR and NaO2S(CH2)4SS(CH2)4SO2Na.
Effect of Solvation on the Nucleophilic Reaction of Stable Carbanions with Diaryl Disulfides
Gilbert, H. F.
, p. 7059 - 7065 (2007/10/02)
Stable carbanions react with diaryl disulfides in aqueous solution by direct displacement (SN2) reaction to yield an arylthiol anion and the corresponding sulfide as products.The reaction of 1,3-dicarbonyl carbanions with 5,5'-dithiobis(2-nitrobenzoic acid) is characterized by Broensted βC value of 0.5.Nitroalkane carbanions react 102-104 slower than 1,3-dicarbonyl carbanions of the same pK and are correlated by a Broensted βC of 0.95.The second-order rate constants for the reaction of nitroalkane carbanions increase by factors of 104-106 as the solvent is changed from water to dimethyl sulfoxide.Smaller increases are observed in the rate constants for reaction of 2,4-pentadienone carbanion (102) and malonitrile carbanion (100.6) with the same sulfide.A linear correlation is found between log (kMe2SO4/kHOH) and the increase in pK for the carbon acid ionization on changing the solvent from water to dimethyl sulfoxide.The effect is attributed to large differences in ground-state carbanion solvation which are reduced or absent in the transition state.Parallels are drawn between the nucleophilic reaction of stable carbanions with diaryl disulfides and proton-transfer reactions of the same carbanions.
