- An efficient, one-pot and CuCl-catalyzed route to the synthesis of symmetric organic disulfides via domino reactions of thioacetamide and aryl (alkyl) halides
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In this article, a simple, general and novel method for the synthesis of diaryl (dialkyl) disulfides from aryl (alkyl) halides is described. This is a convenient approach that involves the use of commercially available and inexpensive thioacetamide as a sulfur transfer reagent in the domino process for the synthesis of symmetric organic disulfides. Copyright
- Soleiman-Beigi, Mohammad,Hemmati, Maryam
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p. 734 - 736
(2013/12/04)
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- Gas-phase reaction of 2-chlorothiophene with hydrogen sulfide in the presence of alcohols
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The effect of methanol and ethanol on the route of the gas-phase reaction of 2-chlorothiophene with hydrogen sulfide, leading to 2-thiophenethiol and to bis(2-thienyl) sulfide, has been investigated. It was found that methanol significantly enhances this
- Deryagina,Sukhomazova,Levanova
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- Reactions of Halothiophenes with Arene- and Hetarenethiols
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Reactions of halothiophenes with sulfanyl radicals generated from arene- and hetarenethiols at 140-200°C have been studied for the first time. The reactions result in replacement of halogen in 2-bromothiophene and 2,5-dichloro-, 2-bromo-5-chloro-, and 2,5-dibromothiophenes. The two halogen atoms in dihalothiophenes are replaced only by phenylthio radical generated from benzenethiol. 4-Methylbenzenethiol and naphthalene-1-thiol react with halothiophenes most selectively, yielding corresponding unsymmetrical sulfides. The reactions with 2-thiophenethiol are accompanied by self-condensation to give dithienyl sulfide. The reactions of arene- and hetarenethiols with halothiophenes provide a synthetic route to unsymmetrical sulfides of the thiophene series, which are difficult to obtain by other methods, and allow prediction of the behavior of other sulfanyl radicals in similar reactions.
- Deryagina,Papernaya,Klyba,Voronkov
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p. 1296 - 1298
(2007/10/03)
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- THERMAL TRANSFORMATIONS OF ALLYL 2-THIENYL SULFIDE AND SELENIDE
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In the gas phase at 350-410 deg C allyl 2-thienyl sulfide is converted to thiophene-2-thiol, di(2-thienyl) sulfide, and 2-methylthienothiophene.In the presence of acetylene thienothiophene is formed in addition to these products.Allyl 2-thienyl selenide is converted quantitatively to 2,3-dihydro-2-methylselenophenothiophene during fractional distillation in vacuo.Thiophene, di(2-thienyl) selenide, di(2-thienyl) diselenide, thiophene-2-selenol, and 2-methylselenophenothiophene are formed in addition to these compounds in the thermolysis ofallyl thienyl selenide in the gas phase.In the presence of acetylene the thermal decomposition of allyl thienyl selenide is accompanied by the formation of selenophene.
- Korchevin, N. A.,Sukhomazova, E. N.,Russavskaya, N. V.,Turchaninova, L. P.,Sigalov, M. V.,et al.
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p. 1049 - 1052
(2007/10/02)
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- FORMATION OF THIENOTHIOPHENES IN THE HIGH TEMPERATURE REACTION OF 2-CHLOROTHIOPHENE WITH COMPOUNDS CONTAINING THE C2H5S GROUP
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The high temperature gas-phase reaction of 2-chlorothiophene with a mixture of diethyl disulfide and diethyl trisulfide constitutes a simple one-step synthesis of a 4:1 mixture of thioeno- and thieno-thiophenes.Their total yield depends on the nature of the donor of the ethylthio group.
- Korchevin, N. A.,Sukhomoazova, E. N.,Turchaninova, L. P.,Efremova, G. G.,Kalinina, N. A.,et al
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p. 857 - 860
(2007/10/02)
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- NEW SYNTHESIS OF 1,2,5-SELENADIAZOLES
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A new synthesis of 1,2,5-selenadiazoles which starts from unsubstituted or monosubstituted 1,2,5-thiadiazoles and Grignard reagents is described and the mechanism of the reaction discussed.
- Bertini, Vincenzo,Munno, Angela De,Picci, Nevio,Lucchesini, Francesco,Pocci, Marco
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p. 2153 - 2158
(2007/10/02)
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- HIGH-TEMPERATURE ORGANIC SYNTHESIS. XXVII. REACTIONS OF ALKANETHIONES WITH THE CHLORINE DERIVATIVES OF BENZENE, THIOPHENE, AND NAPHTHALENE
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Alkanethiols react effectively with chlorobenzene, its derivatives, 1-chloronaphthalene, and 2-chlorothiophene at 600-660 deg C with the preferential formation of the corresponding aromatic or heteroatomic thiols.Ethanethiol is most reactive.When it is used instead of hydrogen sulfide in reactions with chlorobenzene or its 4-substituted derivatives, the yield of the aromatic thiols, from which the phenylthiyl radicals are generated with greater difficulty, increases more sharply than the yield of the thiophenols, which generate the more stable 4-XC6H4S radicals.The side products of the reactions are the corresponding diaryl sulfides, thiophene, benzothiophene, and toluene.
- Voronkov, M. G.,Deryagina, E. N.,Sukhomazova, E. N.
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p. 755 - 760
(2007/10/02)
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- THERMAL HYDROTHIOLYSIS OF DI(2-THIENYL)SULFIDE IN THE GASEOUS AND LIQUID PHASE
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At 500-600 deg C, di(2-thienyl)sulfide is converted to thiophene, thiophene thiols, dithienyls, and dithienothiophenes, and isomerized to 2,3-dithienylsulfide.Hydrogen sulfide accelerates these reactions significantly.In the liquid phase the thermal conversion of di(2-thienyl)sulfide takes place only with the participation of elemental sulfur or in the system sulfur-hydrogen sulfide.Thiophene and diethienothiophenes are not formed in this case, while isomerization occurs to a large degree.The observed thermal conversions of di(2-thienyl)sulfide are based on the addition of thiyl radicals to the double bonds of the thiophene ring and to the sulfide sulfur atom.
- Voronkov, M. G.,Deryagina, E. N.,Papernaya, L. K.,Sukhomazova, E. N.,Korchevin, N. A.,Efremova, G. G.
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p. 1301 - 1306
(2007/10/02)
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- HIGH-TEMPERATURE ORGANIC SYNTHESIS. XVII. REACTION OF CHLOROBENZENE AND ITS DERIVATIVES WITH DIALKYL DISULFIDES
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The products from the reaction of chlorobenzene with dialkyl disulfides in the gas phase at 550-650 deg C are benzene, thiophenol, diphenyl sulfide, and also toluene, thiophene, and benzothiophene.Diethyl disulfide is most reactive.Its copyrolysis with chlorobenzene is distinguished by high selectivity for the formation of thiophenol, the yield of which amounts to 60percent.In the reaction of substituted chlorobenzenes and also 2-chlorothiophene and 1-chloronaphthalene with diethyl disulfide the corresponding thiols were obtained with high yields.Two paths for the formation of thiophene during the pyrolysis of dialkyl disulfide were established, i.e., from vinyl hydrosulfide and S-butyl radical.The last reaction is realized at a high rate.
- Voronkov, M. G.,Deryagina, E. N.,Sukhomazova, E. N.
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p. 1516 - 1522
(2007/10/02)
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