- The Reactions of the 1,2-Ethanediylbis(trithiocarbonic acid) Dianion with Several Electrophilic Reagents
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It has been found that the reaction of the 1,2-ethanediylbis(trithiocarbonic acid) dianion with haloacetic esters, chloromethyl ethers, and chloromethyl sulfides in tetrahydrofuran proceeds smoothly to afford 1,2-ethanediylbis(alkoxycarbonylmethyl trithiocarbonates), 1,2-ethanediylbis(alkoxymethyl trithiocarbonates) and bis(alkylthiomethyl) trithiocarbonates plus ethylene trithiocarbonate respectively.
- Tanimoto, Shigeo,Oida, Tatsuo,Kokubo, Toshio,Okano, Masaya
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- A convenient one-pot method for the synthesis of symmetrical dialkyl trithiocarbonates using NH4OAc under mild neutral conditions
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A facial, new, one-pot method for the preparation of symmetrical organic trithiocarbonates from various alkyl halides and carbon disulfide is described. This is a convenient, clean, and mild procedure, which involves the use of the neutral, nontoxic, commercially available, and inexpensive reagent NH4OAc in the preparation of the trithiocarbonate ion from carbon disulfide.
- Arzehgar, Zeinab,Ahmadi, Hosna
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p. 303 - 306
(2018/11/01)
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- Reaction of three cyclic thioester ligands with triiron dodecacarbonyl and possible reaction mechanisms
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Abstract : Three cyclic thioesters of the formula “-SCH2CH2SCO(CH2)n-” (L1, n = 0 ? L2, = 1 , L3, n = 2) and their reactions with Fe 3(CO) 12 are reported. All the reactions produced a known diiron complex, [Fe 2(μ - S 2C 2H 4) (CO) 6] (1), which suggested that in the reactions, cleavage of C-S bond to generate “SCH 2CH 2S ” fragment is a common pathway for all the three ligands. In the case of ligand L2, a new complex 2, [Fe 2{ μ - SC 2H 4(SCH 2) - κ } (CO) 6] was isolated and structurally characterized. In the reaction of ligand L3, an unknown iron carbonyl product was isolated in addition to complex 1. Although its precise structure was not established due to its instability and low yield, its infrared spectrum and decomposing into complex 1 implied that the product may be a cluster with higher nuclearity. The experimental observations suggested that with the increase of the ring size of the cyclic thioester ligands, further bond cleavages were involved in the reaction in addition to that leading to complex 1. GRAPHICAL ABSTRACT: SYNOPSIS Reaction of cyclic thioester ligands with triiron dodecacarbonyl leads to scission of C-S (C) bond which is initiated by the coordination of the S atom to the Fe atom. The larger the ring size of the ligand, the more diverse are the bond cleavages. [Figure not available: see fulltext.].
- Xiao, Zhiyin,Wang, Yongli,Chen, Xueyuan,Long, Jiao,Wei, Zhenhong
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p. 1595 - 1601
(2017/11/03)
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- Atom economical synthesis of di- and trithiocarbonates by the lithium: Tert -butoxide catalyzed addition of carbon disulfide to epoxides and thiiranes
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Alkali metal alkoxides were studied as catalysts for the addition of CS2 to epoxides. A screening of several commercially available alkoxides revealed lithium tert-butoxide as an active and selective catalyst for this reaction. The influence of different reaction parameters as well as the substrate scope under optimized reaction conditions has been studied. Terminal and highly substituted epoxides as well as thiiranes were converted. In total 28 products were prepared and isolated in yields up to 95%. Notably, the reactions were performed under mild conditions without additional solvents. The regio- and stereoselectivity of the reaction has been studied e.g. by converting (R)-styrene and (R)-propylene oxide. Moreover, the test reaction was monitored by 13C NMR and a plausible mechanism for the conversion of terminal and internal epoxides is given. This proposal is in agreement with the observed regio- and stereoselectivity of the reaction.
- Diebler,Spannenberg,Werner
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supporting information
p. 7480 - 7489
(2016/08/16)
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- Superbasic system CsOH/DMSO as a reagent for a fast one-step synthesis of symmetrical dialkyl trithiocarbonates
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Symmetrical dialkyl trithiocarbonates were readily synthesized in excellent yields by one-step reaction of carbon disulfide and various alkyl halides under mild reaction conditions in the presence of cesium hydroxide as a super basic system. This method provides a synthesis of symmetrical dialkyl trithiocarbonates in short reaction times without the use of highly toxic starting materials.
- Yousefi, Ali
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p. 672 - 677
(2015/11/18)
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- An Efficient and Straightforward Access to Symmetrical Dialkyl Trithiocarbonates Using a Basic Task-Specific Ionic Liquid and Carbon Disulfide
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We report an efficient one-pot route for the synthesis of symmetrical dialkyl trithiocarbonates from alkyl halides using carbon disulfide and a basic ionic liquid 1,1′-bis-methyl-3, 3-methylene-bisimidazolium dihydroxide as a reagent and phase-transfer catalyst.
- Sayyahi, Soheil,Moonesi, Saeid,Fallah-Mehrjardi, Mehdi
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p. 1718 - 1722
(2015/11/02)
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- An efficient one-pot approach to the synthesis of symmetric trithiocarbonates from carbon disulfide and alkyl halides using imidazole
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A novel method is reported for the synthesis of symmetric dialkyl and cyclic (5, 6 and 7 member) trithiocarbonates from alkyl halides and carbon disulfide in the presence of imidazole and water in DMSO under mild reaction conditions. Imidazole is used as an inexpensive, non-toxic and readily available catalyst in this procedure.
- Soleiman-Beigi, Mohammad,Taherinia, Zahra
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p. 470 - 476
(2014/08/18)
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- K3PO4-mediated one-pot synthesis of symmetrical trithiocarbonates
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A new procedure has been developed for synthesis of symmetrical trithiocarbonates by one-pot reaction of carbon disulfide, and various alkyl halides in dimethylformamide using K3PO4 as an inexpensive and effective reagent.
- Movassagh, Barahman,Alapour, Saba
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p. 222 - 226
(2013/08/26)
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- A novel one-step synthesis of symmetrical dialkyl trithiocarbonates in the presence of phase-transfer catalysis
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Symmetrical trithiocarbonates were directly obtained, in moderate to excellent isolated yields, by the reaction of various primary, secondary, allylic and benzylic halides or alkyl tosylates with a suspension of granulated KOH and alumina in CS2 under phase-transfer catalysis. In this manner, cyclic trithiocarbonates such as 1,3-dithiolane-2-thione can also be prepared without formation of any polymeric by-products.
- Kiasat, Ali Reza,Mehrjardi, Mehdi Fallah
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experimental part
p. 639 - 642
(2009/05/11)
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- Basic Al2O3 as an efficient heterogeneous reagent for the synthesis of symmerical dialkyl trithiocarbonates
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This work deals with reaction of alkyl halides with carbon disulfide in the presence of basic alumina as heterogeneous and reusable reagent. It afforded symmetrical dialkyl trithiocarbonate in moderate to excellent isolated yields. Reaction of 1,2-dichloro ethane with carbon disulfide also proceeded in a similar manner to give a five-membered cyclic trithiocarbonate without formation of any polymeric by-product. Copyright Taylor & Francis Group, LLC.
- Kiasat, Ali Reza,Kazemi, Foad,Savari, Ali
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p. 1057 - 1063
(2008/09/18)
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- C-H activation with elemental sulfur: Synthesis of cyclic thioureas from formaldehyde aminals and S8
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The C-H activation of cyclic formaldehyde aminals LCH2 (L = RNCH2CH2CH2-NR and RNCH2CH2-NR, R = Me, Et, iPr, tBu, or Ph) with S8 proceeds at unusually low temperatures (T 2S. The reaction constitutes a new, solvent-free method for the synthesis of thioureas that eliminates the toxic and highly flammable CS2. For R = tBu, the ionic carbenium thiocyanates [LCH]+ SCN- dominate the product spectrum and the respective thioureas are obtained in low yield. The reactivity of the analogous sulfur and oxygen ring systems towards S8 was investigated. 1,3-Dithiolane is cleanly converted into 1,3-dithiolane-2-thione (S8, 14 d, 190°C) and resembles the cyclic formaldehyde aminals in this respect. 1,3-Dioxolane (L = OCH2CH2O) is completely inert towards sulfur even under forceful reaction conditions (190°C, 14 d). The formation of thioureas from aminals was investigated at the CBS-4 and B3LYP/6-31G(d) levels of theory.
- Denk, Michael K.,Gupta, Shilpi,Brownie, John,Tajammul, Sabiha,Lough, Alan J.
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p. 4477 - 4486
(2007/10/03)
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- Synthesis of Symmetrical Dialkyl Trithiocarbonates Using a Polymer Supported System
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Symmetrical dialkyl trithiocarbonates were readily snythesized in excellent yields from alkyl halides and carbon disulfide under mild reaction condition in the presence of a regenerable hydroxide form of an anion exchange resin.
- Tamami, Bahman,Kiasat
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p. 454 - 455
(2007/10/03)
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- An Inadvertent Synthesis of Cyclic and Acyclic Trithiocarbonates under Phase-transfer Conditions
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The formation of trithiocarbonates (7, 8) and ketene dithioacetals (4) from (imidazol-1-yl)acetonitrile (1a) and ethyl(imidazol-1-yl)acetate (1b) under both normal and phase-transfer conditions is delineated.
- Ram, Vishnu J.,Singh, Sunil K.,Nath, Mahendra,Srivastava, Pratibha
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- A Novel One-step Synthesis of Symmetrical Dialkyl Trithiocarbonates
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Symmetrical dialkyl trithiocarbonates were obtained directly, in excellent yields, by reaction of primary or secondary alkyl, benzyl or allyl halides with KOH and carbon disulfide in anhydrous THF; compounds such as methyl 4-bromomethylbenzoate and chloromethyl methyl ether can also be tolerated under the reaction conditions to provide trithiocarbonates 6 and 9 in acceptable yields.
- Leung, Man-kit,Hsieh, Dung-Ting,Lee, Kang-Hwa,Liou, Jia-Chie
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p. 478 - 479
(2007/10/03)
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- Synthesis of vicinal alkanedithiols
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The invention relates to the manufacture of vicinal alkanedithiols from the corresponding alkylene trithiocarbonates. The method according to the invention consists in treating alkylene trithiocarbonate with an alkaline sulfide, followed by acidification of the reaction medium. The method is particularly well-suited for the synthesis of ethanedithiol from ethylene trithiocarbonate.
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- Convenient Synthesis of Cyclic Trithiocarbonates from 1,2- or 1,3-Dihaloalkanes and Sodium Trithiocarbonate in the Presence of Phase-Transfer Catalyst
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Cyclic trithiocarbonates, such as 1,3-dithiolane-2-thiones and 1,3-dithiane-2-thiones, were conveniently synthesized by treating 1,2- or 1,3-dihaloalkanes with sodium trithiocarbonate in the presence of a phase-transfer catalyst.
- Sugawara, Akira,Sato, Tsukasa,Sato, Ryu
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p. 339 - 341
(2007/10/02)
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- ONE POT PHASE TRANSFER SYNTHESIS OF TRITHIOCARBONATES FROM CARBON DISULPHIDE AND ALKYL HALIDES
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Symmetrical and cyclic alkyl trithiocarbonates were synthesized by reacting CS2 and 33percent aqueous NaOH with alkyl halides under phase transfer catalysis conditions
- Lee, Albert W. M.,Chan, W. H.,Wong, H. C.
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p. 1531 - 1536
(2007/10/02)
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- EFFICIENT SYNTHESES OF A NEW PENEM ANTIBIOTIC, SODIUM (5R,6S)-2-(2-FLUOROETHYLTHIO)-6-PENEM-3-CARBOXYLATE
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Two useful routes to sodium (5R,6S)-2-(2-fluoroethylthio)-6-penem-3-carboxylate (1) via trithiocarbonate (3) are reported.An intramolecular Wittig reaction of 6 and an oxalimide cyclization of 9 with phosphite are employed as key steps.
- Kawamoto, Isao,Endo, Rokuro,Suzuki, Kosato,Hata, Tadashi
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p. 123 - 128
(2007/10/02)
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- Convenient Synthesis of Alkanediyl Bis(alkyl trithiocarbonate)s from Alkanedithiols with Alkyl Halides and Carbon Disulfide in the Presence of Phase Transfer Catalyst
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Alkanediyl bis(alkyl trithiocarbonate)s were conveniently synthesized by treating alkanedithiols with alkyl halides and carbon disulfide in the presence of a phase transfer catalyst.
- Sugawara, Akira,Hasegawa, Ken,Suzuki, Ken-ichi,Takahashi, Yukio,Sato, Ryu
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p. 435 - 437
(2007/10/02)
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- The Synthesis of 1,3-Dithiolane-2-thione Derivatives
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The reaction of 2,2-dimethylthiirane with carbon disulfide in the presence of triethylamine was accelerated under high pressure to give 4,4-dimethyl-1,3-dithiolane-2-thione nearly quantitatively.The activation volume of this reaction at 40 deg C was estimated to be -41 ml mol-1.The rate of the reaction was proportional to the amount of triethylamine when a limited amount of triethylamine was used.The reaction of 2-methylthiirane, 2-hexylthiirane, 1,2-epithiocyclohexane, and 2-phenylthiirane with carbon disulfide gave the corresponding 1,3-dithiolane-2-thione derivatives in good yields. 2-Chloromethylthiirane was less reactive to carbon disulfide than other thiiranes under high pressure.Tertiary amines such as N,N-dimethylethylamine, pyridine, and N-methylmorpholine were good catalysts of the reaction.
- Taguchi, Yoichi,Yanagiya, Koshin,Shibuya, Isao,Suhara, Yasuo
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p. 727 - 730
(2007/10/02)
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- Phase-Transfer Synthesis of Symmetrical and Unsymmetrical Dialkyl Trithiocarbonates
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Symmetrical and unsymmetrical dialkyl trithiocarbonates having the formula R1S-CS-SR2 (wherein R1 = or R2) were prepared under phase-transfer catalytic conditions by one-pot reactions involving carbon disulfide, sodium sulfide, alkyl halides and alkyl mercaptans.
- Degani, Iacopo,Fochi, Rita,Gatti, Antonella,Regondi, Valeria
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p. 894 - 899
(2007/10/02)
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- A NEW CONVENIENT METHOD FOR THE SYNTHESIS OF 1,3-DITHIOLANE-2-THIONES AND THEIR USE FOR THE SYNTHESIS OF 4,5-DIMETHOXYCARBONYL-1,3-DITHIOLE-2-THIONE
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A preparative method was developed for the synthesis of 1,3-dithiolane-2-thione and 4-phenyl-1,3-dithiolane-2-thione from dibromoethane and 1-phenyl-1,2-dibromoethane and potassium xanthates.It was shown that their reaction with dimethyl acetylenedicarboxylate without a solvent leads to 4,5-dimethoxycarbonyl-1,3-dithiole-2-thione with yields close to quantitative.
- Khodorkovskii, V.Yu.,Poikan, Ya.Ya.,Kreitsberga, Ya.N.,Neiland, O.Ya.
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p. 1224 - 1226
(2007/10/02)
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- BENZYNE-INDUCED FRAGMENTATION REACTIONS OF 1,3-DITHIOLANES
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2-Monosubstituted 1,3-dithiolanes, on reaction with benzyne, undergo two types of fragmentation, one of which gives phenyl vinyl sulfide and thioaldehydes (corresponding aldehydes as the final products) and the other gives phenyl dithiocarboxylates and et
- Nakayama, Juzo,Ozasa, Hiroshi,Hoshino, Masamatsu
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p. 1053 - 1056
(2007/10/02)
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- The Preparation of Cyclic Dithia and Thiaza Compounds by the Reaction of Potassium Carbonate with Heterocumulenes and Alkylene Dibromides or Carbonate Catalyzed by Organostannyl Compounds
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Cyclic 1,3-dithia- and 1,3-thiaza-2-ylidene compounds were obtained by the heterogenous reaction of solid potassium carbonate, a sulfur-containing heterocumulene, such as aryl isothiocyanate, carbon disulfide, or carbonyl silfide, and alkylene dibromides or ethylene carbonate in the presence of bis(tributylstannyl) compounds.The effect of an organostannyl catalyst on these reactions is discussed.
- Fujinami, Tatsuo,Sato, Shinichi,Uchida, Norimasa,Sakai, Shizuyoshi
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p. 1174 - 1177
(2007/10/02)
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- Comparative radioprotective activity of various pentagonal compounds with two heteroatomes
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Various heterocyclic compounds with two heteroatomes were synthesized and their potential radioprotective activity was tested. This study shows the interest of phenylthiazolidines derivatives in chemical radioprotection.
- Robbe,Fernandez,Dubief,et al.
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p. 235 - 243
(2007/10/02)
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- GENERATION OF 1,2-ETHANEBIS(TRITHIOCARBONIC ACID) DIANION FROM 2,2'-BIS-1,3-DITHIOLANE AND ITS REACTION WITH ALKYL HALIDES
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Generation of 1,2-ethanbis(trithiocarbonic acid) dianion from 2,2'-bis-1,3-dithiolane and its reaction with alkyl halides were investigated.
- Tanimoto, Shigeo,Oida, Tatuo,Hatanaka, Kouhei,Sugimoto, Toyonari
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p. 655 - 658
(2007/10/02)
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- Thiocarbonyl Ylide Intermediates Generated by Deprotonation of 2-Phenacylthio- and 2-(p-Bromophenacylthio)-1,3-dithiolylium and 2-(p-Bromophenacylthio)-1,3-dithiolanylium Bromides
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2-(p-Bromophenacylthio)-1,3-dithiolynium bromide, when treated with triethylamine, gave 2-(p-bromophenacylidene)-1,3-dithiole (17percent) and bis-disulfide (72percent).Treatment of 2-phenacylthio-1,3-dithiolylium bromide with triethylamine also gave similar results.On the other hand, 2-(p-bromophenacylthio)-1,3-dithiolanylium bromide yielded 1-(p-bromophenyl)-2-(1,3-dithiolan-2-yl)-2-thioxoethanone (12percent) in addition to 2-(p-bromophenacylidene)-1,3-dithiolane (49percent) contrary to the reported results.These results can best be rationalized by 1,3-cyclization of thiocarbonyl ylide intermediates to the valence tautomeric episulfides.
- Nakayama, Juzo,Takemasa, Toshiro,Hoshino, Masamatsu
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p. 2281 - 2284
(2007/10/02)
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- Thion- und Dithioester, XXIV Synthese von Tetrathiooxalestern
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Reduction of carbon disulfide with potassium in dimethylformamide and subsequent alkylation yields the isotrithiones 2, which have been desulfurised with mercury acetate to give the 1,3-dithiol-2-ones 3. 2a is also available by a stepwise synthesis starting with methyl (methylthio)dithioacetate (6).The photochemical decarbonylation of 4,5-bis(methylthio)-1,3-dithiol-2-one (3a) leads to the formation of dimethyl tetrathiooxalate (11a).In solution 11a is in equilibrium with its dimer 13.Cyclic tetrathiooxalates are probably unstable at room temperature.
- Hartke, Klaus,Kissel, Thomas,Quante, Josef,Matusch, Rudolf
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p. 1898 - 1906
(2007/10/02)
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- Pesticidal compositions containing phosphoric esters and divalent sulphur compounds
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Pesticidal composition comprising: a pesticidal, phosphoric ester the molecule of which has at least one alkyl group of 1 to 3 carbon atoms, 0.05 to 10% of an agent stabilizing the said ester against decomposition by protonisation, together with adjuvants characterized in that the stabilizing agent comprises at least one sulphur compound containing per molecule at least one divalent sulphur atom of which one valence is bonded to an atom chosen from sulphur, carbon, nitrogen, hydrogen, and metals capable of giving a salt, the other valence being bonded to an atom chosen from hydrogen, the carbon atom already noted, a second carbon atom, the nitrogen atom already noted, a second nitrogen atom, the metal atom already noted in the case of a metal of valence greater than one, a second atom of metal and oxygen when the first valence is not attached to an atom of hydrogen, the proportion of sulphur calculated with reference to the weight of the sulphur compound being between 5 and 99%. Process for stabilizing a phosphoric ester of which the molecule possesses at least one alkyl group containing 1 to 3 carbon atoms characterized in that there is added to the phosphoric ester or to a mixture which contains it, 0.05 to 10% calculated on the weight of the phosphoric acid ester of an agent capable of stabilizing the said phosphoric ester against protonisation and comprising at least one sulphur compound such as that defined thereupon.
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