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Шагун, Л. Г.; Дорофеев, И. А.; Ermolyuk, L. P.; Sarapulova, G. I.; Воронков, М. Г.

doi:10.1023/a:1013177313207

Cited by 7 publications

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“…Also mercury(II) and lead(II) dithiolates are known. They arise in the reaction of geminal dithiols with mercury(II) chloride or lead(II) acetate in methanol [25,26].…”

Section: Acid Properties Of Thiols Generation Of Thiolate Anionsmentioning

confidence: 99%

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Synthesis, Structure, and Physicochemical Characteristics of Thiols

Koval

2005

Russ J Org Chem

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“…Also mercury(II) and lead(II) dithiolates are known. They arise in the reaction of geminal dithiols with mercury(II) chloride or lead(II) acetate in methanol [25,26].…”

Section: Acid Properties Of Thiols Generation Of Thiolate Anionsmentioning

confidence: 99%

“…For instance, it was mentioned that hydrogen sulfide addition across C=O and C=S bonds in haloketones[51] and halothioketones[52] afforded unstable geminal dithiols in 8394% yield…”

mentioning

confidence: 99%

Synthesis, Structure, and Physicochemical Characteristics of Thiols

Koval

2005

Russ J Org Chem

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“…The most probable intermediate of the reaction of iodoacetone with hydrogen sulfide is the tetrathiol 4. An additional argument in favor of this suggestion may be the formation of geminal dithiones in quantitative yield on the interaction of ether solutions of α-haloketones with ether solutions of hydrogen sulfide at low temperatures [6][7][8].…”

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confidence: 99%

Synthesis and characteristics of the mass spectra of 2,5-dimercapto-2,5-dimethyltetrahydrothiophene

Шагун

Клыба

Дорофеев

et al. 2007

Chem Heterocycl Compd

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2,5-Dimercapto-2,5-dimethyltetrahyrothiophene was synthesized by the reaction of 1-iodopropan-2-one with hydrogen sulfide in an ether solution of hydrogen chloride at -70˚C. Its structure was established by mass spectrometry, 1 H and 13 C NMR spectroscopy.Reaction of 2,5-hexanedione with hydrogen sulfide in an ethanol solution of hydrogen chloride at -35°C gave a mixture of three compounds: 2,5-dimethylthiophene, 2-mercapto-2,5-dimethyl-2,3-dihydrothiophene, and 2,5-dimercapto-2,5-dimethyltetrahydrothiophene in yields of 33, 3, and 15% respectively [1]. According to [2] the intermediate in the formation of 2,5-dimethylthiophene is 2,5-hexanedithione, while the intermediate for the formation of 2,5-dimercapto-2,5-dimethyl-2,3-tetrahydrothiophene is 2,2,5,5-hexanetetrathiol. That 2,5-dimercapto-2,5-dimethyl-2,3-tetrahydrothiophene may be a product of intramolecular cyclization of 5,5-dimercaptohexan-2-thione was not excluded. The synthesis and possible conversions of 2,5-hexanedithione and 2,2,5,5-hexanetetrathiol have been discussed previously [3,4].In a study of the reaction of 1-iodopropan-2-one (1) with hydrogen sulfide in an ether solution of hydrogen chloride at -70°C, we established that the reaction began with the separation of iodine and the formation of 2,5-hexanedione (2), the hydrothiolysis might lead to the formation 5,5-dimercaptohexane-2-thione (3) and 2,2,5,5-hexanetetrathiol (4). 2,3-Dimercapto-2,5-dimethyltetrahydrothiophene (5) is formed in 75% yield by intramolecular cyclization of the thione (3) and tetrathiol (4) intermediates. Me I O Me O Me O Me Me S SH SH Me SH SH Me SH SH S SH Me S H Me 1 + H 2 S HCl, Et 2 O -I 2 2 H 2 S/HCl -2H 2 O + 3 4 5 __________________________________________________________________________________________

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ChemInform Abstract: 1‐Haloethane‐2,2‐dithiols.

et al. 2002

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2002 mercaptans, thioethers mercaptans, thioethers (benzene compounds) Q 0580 20 -063 1-Haloethane-2,2-dithiols. -Optimal conditions for the synthesis of the title compounds (II) by low-temperature acid-catalyzed hydrosulfurization of corresponding 1-haloketones (I) are established. Attempted hydrosulfurization of nitrophenyl bromomethyl ketone (III) affords the corresponding thioketone (IV). -(SHAGUN, L. G.; DOROFEEV, I. A.; ERMOLYUK, L. P.; SARAPULOVA, G. I.; VORONKOV, M. G.; Russ.

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Cited by 7 publications

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Synthesis, Structure, and Physicochemical Characteristics of Thiols

Synthesis, Structure, and Physicochemical Characteristics of Thiols

Synthesis and characteristics of the mass spectra of 2,5-dimercapto-2,5-dimethyltetrahydrothiophene

ChemInform Abstract: 1‐Haloethane‐2,2‐dithiols.

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