Selective and Simple Phase Transfer Catalyzed Synthesis of Disulfides from Thiols

Абеле, Э.; Абеле, Р.; Lukevics, É.

doi:10.1039/a903845k

Cited by 24 publications

(4 citation statements)

References 21 publications

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“…On the basis of the above experimental results and the work reported by us 13 and Abele et al, 20 a possible mechanism for the formation of thiourea/thiones 2 and thiuram disulfides 4 was proposed (Scheme 1). Initially, nucleophilic attack of the mesomeric thioanion of I at the bromine atom of carbon tetrabromide produces the sulfenyl bromide II.…”

Section: Equationmentioning

confidence: 69%

Carbon Tetrabromide Promoted Reaction of Amines with Carbon Disulfide: Facile and Efficient Synthesis of Thioureas and Thiuram Disulfides

Liang¹,

Tan²,

Piao³

et al. 2008

Synthesis

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A novel carbon tetrabromide promoted one-pot reaction of amines and carbon disulfide under mild conditions has been developed, which provides a straightforward and efficient access to thioureas and thiuram disufides, depending on the nature of the amines employed. The promotion effect is explained as the transient formation of a sulfenyl bromide intermediate from dithiocarbamate and carbon tetrabromide during the reaction.

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Section: Equationmentioning

confidence: 69%

Carbon Tetrabromide Promoted Reaction of Amines with Carbon Disulfide: Facile and Efficient Synthesis of Thioureas and Thiuram Disulfides

Liang¹,

Tan²,

Piao³

et al. 2008

Synthesis

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“…Reagents such as of MnO 2 , 7 dichromates, 8 borohydride exchange resin, 9 DMSO/alumina, 10 CBr 4 /K 2 CO 3 /18-crown-6/ benzene, 11 NaIO 3 /alumina, 12a molybdate sulfuric acid/NaNO 2 , 12b tetramethylammonium uorochromate, 13 cerium(IV) salt, 14 copper salt, 15 rhenium-sulfoxide complex, 16a rhodium(I) complex, 16b have been utilized for oxidation of thiols to disuldes. However, some of the reported reagents suffer from disadvantages such as toxicity, high price of some reagents, instability, hygroscopicity, low selectivity, long reaction time, difficulty of preparation, need for a large excess of the reagent and the overoxidation of the disulde to thiosulnates and derivatives.…”

Section: Introductionmentioning

confidence: 99%

Cubic Ag₂O nanoparticle incorporated mesoporous silica with large bottle-neck like mesopores for the aerobic oxidative synthesis of disulfide

et al. 2015

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“…[4][5][6][7] The most common approach for the synthesis of disulfides is the oxidation of thiols. Various oxidants with catalysts have been used, including K 3 PO 4 , 8 halogens, [9][10][11][12] NH 4 OH, 13 and H 2 O 2 . 14 Although these conventional methods produce disulfide products in high yields, they often involve complicated purification processes, hazardous chemicals, and expensive metalcontaining reagents or catalysts.…”

Section: Introductionmentioning

confidence: 99%

Photooxidative Coupling of Thiophenol Derivatives to Disulfides

Kim

Yoon

2010

J. Phys. Chem. A

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Disulfide bonds play an important role in determining the structure and stability of proteins and nanoparticles. Despite extensive studies on the oxidation of thiols for the synthesis of disulfides, little is known about the photooxidation of thiols, which may be a clean, safe, and economical alternative to the use of harmful and expensive metal-containing oxidants and catalysts. In this paper, we report the photooxidative coupling of thiophenol derivatives to disulfides. Para-substituted thiophenol derivatives, p-SHC(6)H(4)X (X = NO(2), COOH, Cl, and OCH(3)), are irradiated, and disulfides, X(2)(C(6)H(4))(2)S(2), are identified as the major photoproducts using Raman, UV-vis, IR, and NMR spectroscopies. For p-nitrothiophenol (pNTP), 4,4'-dinitrodiphenyldisulfide (DNDPDS) is produced in 81% yield. The product yield changes with pH, being the highest at pH ≈ 5, suggesting that both neutral thiol and anionic thiolate forms of pNTP are required for the photoreaction to occur. Excitation at 455 nm, at which the thiolate form of pNTP absorbs strongly, leads to the largest yield of DNDPDS, whereas very little DNDPDS is formed by excitation of the thiol form of pNTP at 325 nm. Our observations suggest that the photooxidation occurs via collisions of the electronically excited thiolate form of pNTP with the surrounding neutral thiol forms of pNTP. The photooxidation reaction happens regardless of the electron-withdrawing or electron-donating properties of the substituents if the pH and excitation wavelengths are properly chosen. The versatility of light and generality of the photooxidative coupling reaction of thiophenol derivatives may open new possibilities for selective and site-specific photocontrol of disulfide bond formation in biology and nanomaterial science as well as in synthetic chemistry.

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Selective and Simple Phase Transfer Catalyzed Synthesis of Disulfides from Thiols

Abstract: Two novel methods of synthesis of disulfides from thiols or their Na salts in the phase transfer catalytic system CBr 4 /18-crown-6/benzene or toluene are developed and the products isolated in 67^88% yields.

Cited by 24 publications

References 21 publications

Carbon Tetrabromide Promoted Reaction of Amines with Carbon Disulfide: Facile and Efficient Synthesis of Thioureas and Thiuram Disulfides

Carbon Tetrabromide Promoted Reaction of Amines with Carbon Disulfide: Facile and Efficient Synthesis of Thioureas and Thiuram Disulfides

Cubic Ag₂O nanoparticle incorporated mesoporous silica with large bottle-neck like mesopores for the aerobic oxidative synthesis of disulfide

Photooxidative Coupling of Thiophenol Derivatives to Disulfides

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Selective and Simple Phase Transfer Catalyzed Synthesis of Disulfides from Thiols

Abstract: Two novel methods of synthesis of disulfides from thiols or their Na salts in the phase transfer catalytic system CBr 4 /18-crown-6/benzene or toluene are developed and the products isolated in 67^88% yields.

Cited by 24 publications

References 21 publications

Carbon Tetrabromide Promoted Reaction of Amines with Carbon Disulfide: Facile and Efficient Synthesis of Thioureas and Thiuram Disulfides

Carbon Tetrabromide Promoted Reaction of Amines with Carbon Disulfide: Facile and Efficient Synthesis of Thioureas and Thiuram Disulfides

Cubic Ag2O nanoparticle incorporated mesoporous silica with large bottle-neck like mesopores for the aerobic oxidative synthesis of disulfide

Photooxidative Coupling of Thiophenol Derivatives to Disulfides

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Cubic Ag₂O nanoparticle incorporated mesoporous silica with large bottle-neck like mesopores for the aerobic oxidative synthesis of disulfide