250-84-0Relevant articles and documents
High-Temperature Organic Synthesis. XLIV. Reaction of 2-Chlorothiophene with the System Dialkyl Disulfide-Acetylene
Deryagina, E. N.,Sukhomazova, E. N.,Levanova, E. P.,Voronkov, M. G.
, p. 857 - 859 (2007/10/03)
A convenient procedure is proposed for simultaneous preparation of thiophene and thienothiophene from readily accessible reactants by thermolysis of 2-chlorothiophene in the system diethyl disulfide-acetylene at 500-700 deg C.Thiophene results mainly from the reaction of acetylene with vinylthio radicals generated by thermal decomposition of diethyl disulfide.Thienothiophene is formed by reaction of acetylene with 2-thienylthio radicals generated by reaction of 2-chlorothiophene with hydrogen sulfide which is a product of thermal decomposition of diethyl disulfide.A mixture of lower dialkyl disulfides (disulfide oil) can be used instead of diethyl disulfide.
THERMAL TRANSFORMATIONS OF ALLYL 2-THIENYL SULFIDE AND SELENIDE
Korchevin, N. A.,Sukhomazova, E. N.,Russavskaya, N. V.,Turchaninova, L. P.,Sigalov, M. V.,et al.
, p. 1049 - 1052 (2007/10/02)
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.
HIGH-TEMPERATURE ORGANIC SYNTHESIS XXXII. REACTION OF ACETYLENE WITH LOWER DIALKYL POLYSULFIDES
Voronkov, M. G.,Deryagina, E. N.,Ostroukhova, L. A.,Korchevin, N. A.,Sukhomazova, E. N.,et al.
, p. 2320 - 2322 (2007/10/02)
Dimethyl disulfide and diethyl di-, tri-, and tetrasulfides or their mixtures react with acetylene in the gas phase at 470-520 deg C with the formation of thiophene and isomeric thienothiophenes as the main products (with overall yields of up to 85percent).The reaction mechanism, involving the formation of vinylthiyl radicals, is discussed.
FORMATION OF THIENOTHIOPHENES IN THE HIGH TEMPERATURE REACTION OF 2-CHLOROTHIOPHENE WITH COMPOUNDS CONTAINING THE C2H5S GROUP
Korchevin, N. A.,Sukhomoazova, E. N.,Turchaninova, L. P.,Efremova, G. G.,Kalinina, N. A.,et al
, p. 857 - 860 (2007/10/02)
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.
HIGH-TEMPERATURE ORGANIC SYNTHESIS. XXVII. REACTIONS OF ALKANETHIONES WITH THE CHLORINE DERIVATIVES OF BENZENE, THIOPHENE, AND NAPHTHALENE
Voronkov, M. G.,Deryagina, E. N.,Sukhomazova, E. N.
, p. 755 - 760 (2007/10/02)
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.
HIGH-TEMPERATURE ORGANIC SYNTHESIS. XVII. REACTION OF CHLOROBENZENE AND ITS DERIVATIVES WITH DIALKYL DISULFIDES
Voronkov, M. G.,Deryagina, E. N.,Sukhomazova, E. N.
, p. 1516 - 1522 (2007/10/02)
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.
HIGH - TEMPERATURE ORGANIC SYNTHESIS. XIII. THE REACTIONS OF HYDROGEN SULFIDE WITH 1,2-DICHLOROETHYLENE
Perevalova, V. I.,Bannikova, O. B.,Deryagina, E. N.,Voronkov, M. G.
, p. 355 - 361 (2007/10/02)
1,2-Dichloroethylene reacts with hydrogen sulfide in the gas phase at 420 - 520 deg C in an empty quartz tube, forming bis(β-chlorovinyl)sulfide (geometric isomers), 2- and 3-chlorothiophene, 2,4-dichlorothiophene, 2- and 3-thienyl β-chlorovinyl sulfides (cis and trans isomers), cis-4-chloro-2-thienyl β-chlorovinyl sulfide, and thieno- and thienothiophenes.The yields of these compounds depend on the reaction conditions (temperature, contact time, ratio of initial reagents).At 480 deg C in an excess of 1,2-dichloroethylene the yield of the mixture of2- and 3-chlorothiophene amounts to 25percent (ratio 3 : 1).
