Synthesis of Symmetrical Dialkyl Trithiocarbonates Using a Polymer Supported System

Tamami, Bahman; Kiasat, Ali Reza

doi:10.1039/a800161h

Cited by 43 publications

(27 citation statements)

References 11 publications

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“…Synthesis of CTTC 1 A few cyclic trithiocarbonates, [13,[15][16][17] such as 1,3-dithiolane-2-thione and 1,3-dithiane-2-thione, have been synthesized by different approaches, but none of them could be used as RAFT agents because of their structural dissimilarities to known active RAFT agents. CTTC is not simple to prepare due to the formation of polytrithiocarbonate as a major by-product.…”

Section: Resultsmentioning

confidence: 99%

“…The first method involves dialkylation of trithiocarbonate anion with alkyl halides in a two-phase system using an onium salt as a phase-transfer agent, while the second method reports an efficient one-step synthesis of symmetrical dialkyl trithiocarbonates directly from carbon disulfide and alkyl halides using a commercially available hydroxyl form of an anion-exchange resin. [13,15] Both methods were used in attempts to prepare 1 with 1,4-dibromo-1,4-diphenylbutane as dihalide. However, only the first method using phase-transfer catalysis gave 1 in 30% yield.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of Multiblock Polymer Containing Narrow Polydispersity Blocks

Hong

Wang

Fan

2005

Macromol. Rapid Commun.

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Summary: We have developed a new strategy to prepare multiblock polymers and copolymers via one‐ or two‐step polymerization using a polymerizable cyclic trithiocarbonate (CTTC), 4,7‐diphenyl‐[1,3]dithiepane‐2‐thione. CTTC undergoes ring‐opening process to incorporate a trithiocarbonate moiety. The trithiocarbonate moiety in turn, functions as a reversible addition fragmentation chain transfer (RAFT) agent. Through this mechanism, multiblock polystyrenes and polystyrene‐block‐ poly(butyl acrylate) copolymers containing various narrow polydispersity blocks can be prepared.Integrated process of ring‐opening and RAFT polymerizations involving cyclic trithiocarbonates.magnified imageIntegrated process of ring‐opening and RAFT polymerizations involving cyclic trithiocarbonates.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Synthesis of Multiblock Polymer Containing Narrow Polydispersity Blocks

Hong

Wang

Fan

2005

Macromol. Rapid Commun.

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“…[9] Dry anion exchange resin (50 g, OH -form, Shanghai Resin Ltd.) was added to carbon disulfide (100 mL) and stirred at room temperature for about 5 min. The color of the resin changed from light yellow to deep red.…”

Section: Synthesis Of Dibenzyl Trithiocarbonatementioning

confidence: 99%

60Co γ-Irradiation-Initiated “Living” Free-Radical Polymerization in the Presence of Dibenzyl Trithiocarbonate

Bai¹,

You²,

Pan³

2001

Macromol. Rapid Commun.

122

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The free‐radical polymerization of vinyl monomers in the presence of dibenzyl trithiocarbonate (DBTTC) and under 60Co γ‐irradiation is of living character. Under 60Co irradiation, the bonds between benzyl group and sulfur were cleaved, benzyl radicals initiate the polymerization. The propagating radical together with trithiocarbonate radicals form a dormant polymer chain. The fast equilibrium between propagation radical and dormant polymer chain controls the polymerization.

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“…Indeed, the aqueous solutions containing the CS 3 2− anion have a red-blood color. [41][42][43] The UV-Visible of the CS 3 2− aqueous solution displays two bands at 416 and 502 nm ascribed to the signatures of the n → π * transition of sulfur (Fig. 7).…”

Section: Upon Dissolution Of Csmentioning

confidence: 99%

Understanding chemical reactions of CO2 and its isoelectronic molecules with 1-butyl-3-methylimidazolium acetate by changing the nature of the cation: The case of CS2 in 1-butyl-1-methylpyrrolidinium acetate studied by NMR spectroscopy and density functional theory calculations

Cabaço¹,

Besnard

Chávez

et al. 2014

The Journal of Chemical Physics

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NMR spectroscopy ( 1 H, 13 C, 15 N) shows that carbon disulfide reacts spontaneously with 1-butyl-1-methylpyrrolidinium acetate ([BmPyrro][Ac]) in the liquid phase. It is found that the acetate anions play an important role in conditioning chemical reactions with CS 2 leading, via coupled complex reactions, to the degradation of this molecule to form thioacetate anion (CH 3 COS − ), CO 2 , OCS, and trithiocarbonate (CS 3 2− ). In marked contrast, the cation does not lead to the formation of any adducts allowing to conclude that, at most, its role consists in assisting indirectly these reactions. The choice of the [BmPyrro] + cation in the present study allows disentangling the role of the anion and the cation in the reactions. As a consequence, the ensemble of results already reported on (2), and CO 2 - [Bmim][Ac] (3) systems can be consistently rationalized. It is argued that in system (1) both anion and cation play a role. The CS 2 reacts with the acetate anion leading to the formation of CH 3 COS − , CO 2 , and OCS. After these reactions have proceeded the nascent CO 2 and OCS interact with the cation to form imidazolium-carboxylate ([Bmim] CO 2 ) and imidazoliumthiocarboxylate ([Bmim] COS). The same scenario also applies to system (2). In contrast, in the CO 2 - [Bmim] [Ac] system a concerted cooperative process between the cation, the anion, and the CO 2 molecule takes place. A carbene issued from the cation reacts to form the [Bmim] CO 2 , whereas the proton released by the ring interacts with the anion to produce acetic acid. In all these systems, the formation of adduct resulting from the reaction between the solute molecule and the carbene species originating from the cation is expected. However, this species was only observed in systems (2) and (3). The absence of such an adduct in system (1) has been theoretically investigated using DFT calculations. The values of the energetic barrier of the reactions show that the formation of [Bmim] CS 2 is unfavoured and that the anion offers a competitive reactive channel via an oxygensulphur exchange mechanism with the solute in systems (1) and (2). © 2014 AIP Publishing LLC.

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Synthesis of Symmetrical Dialkyl Trithiocarbonates Using a Polymer Supported System

Cited by 43 publications

References 11 publications

Synthesis of Multiblock Polymer Containing Narrow Polydispersity Blocks

Synthesis of Multiblock Polymer Containing Narrow Polydispersity Blocks

60Co γ-Irradiation-Initiated “Living” Free-Radical Polymerization in the Presence of Dibenzyl Trithiocarbonate

Understanding chemical reactions of CO2 and its isoelectronic molecules with 1-butyl-3-methylimidazolium acetate by changing the nature of the cation: The case of CS2 in 1-butyl-1-methylpyrrolidinium acetate studied by NMR spectroscopy and density functional theory calculations

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