28763-24-8

Usage

InChI:InChI=1/C4H5ClOS2/c5-1-3-2-8-4(7)6-3/h3H,1-2H2

Upstream product

• 75-15-0 carbon disulfide 
• 106-89-8 epichlorohydrin 

Downstream Products

• 1287677-90-0 S-(2-thioxo-1,3-dithiolan-4-yl)methyl-4-(4-fluorophenyl)piperazine-1-carbothioate 
• 1287677-91-1 S-(2-thioxo-1,3-dithiolan-4-yl)methyl-4-(2-methoxyphenyl)piperazine-1-carbothioate 

Relevant academic research and scientific papers

KI–Tetraethylene Glycol Complex as an Effective Catalyst for the Synthesis of Cyclic Thiocarbonates from Epoxides and CS2

An efficient synthesis of cyclic thiocarbonates from epoxides and CS2 under mild reaction conditions was achieved when a KI–tetraethylene glycol complex was used as a readily available and economic catalyst. The effects of various glycols and alkali metal halides were investigated in the present work to clarify the importance of both KI and tetraethylene glycol. The reaction mechanisms for the synthesis of cyclic thiocarbonates are discussed on the basis of the stereochemistry of the products.

Selectively synthesis of cyclic di- and trithiocarbonates by N-heterocyclic carbene/LiCl(Br) catalyzed addition of carbon disulfide to epoxides

Carbon disulfide is an abundant, inexpensive and readily available material. One of the main challenges in the reaction of epoxides with CS2 is to control the chemoselectivity as a variety of compounds would be formed in the reaction. A simple and convenient method toward selectively synthesis of oxathiolane and trithiocarbonate from epoxides with CS2 catalyzed by NHC/LiCl(Br) under the neat conditions has been developed. This catalytic system exhibits excellent activity and selectivity in cycloaddition reactions of carbon disulfide to terminal epoxides.

Atom economical synthesis of di- and trithiocarbonates by the lithium: Tert -butoxide catalyzed addition of carbon disulfide to epoxides and thiiranes

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.

Organocatalytic one-pot synthesis of functionalized 1,3-oxathiolanes and 1,3-thiazolidines

An efficient organocatalytic approach for the synthesis of 1,3-oxathiolanes and 1,3-thiazolidines is reported. In this methodology, conjugated base of nitromethane was employed as a potential organocatalyst to promote cyclization reaction between strained

Bifunctional Ionic Liquids for the Multitask Fixation of Carbon Dioxide into Valuable Chemicals

A series of task-specific ionic liquids (ILs) such as mono-, dicationic, and polymer-supported ILs were synthesized. These ILs were applied as multitasking organocatalysts for transformations of carbon dioxide into valuable chemicals through a range of reactions, including (i) cycloaddition reactions of CO2/CS2 with epoxides to form cyclic carbonates and 1,3-oxathiolane-2-thiones, (ii) transesterification of cyclic carbonates with methanol to form dimethyl carbonate, and (iii) synthesis of quinazoline-2,4(1 H,3 H)-diones and quinazoline-2,4(1 H,3 H)-dithiones from 2-aminobenzonitriles and CO2/CS2. The developed methodology is transition-metal free, solvent free, and additive free. Remarkably, the developed ILs were recyclable in up to seven consecutive cycles; thus, making this protocol green and cost effective.

Synthesis of cyclic di- and trithiocarbonates from epoxides and carbon disulfide catalyzed by N-heterocyclic carbene

The synthesis of cyclic di- and trithiocarbonates from the reaction of epoxides and carbon disulfide catalyzed by N-heterocyclic carbene prepared in situ is described. 1,3-Oxathiolane-2-thiones or 1,3-dithiolane-2-thiones was obtained in high yield with good selectivity when the reactions were carried out with 4 in DMSO at 100°C in the presence of K2CO3. The possible catalytic mechanism was proposed.

Cooperative catalysis with binary Lewis acid-Lewis base system for the coupling of carbon disulfide and epoxides

The cycloaddition of epoxides with carbon disulfide proceeds effectively by using a binary catalyst system of tetradentate Schiff-base aluminum complexes (designated as salenAlX) as Lewis acid in connection with a nucleophilic co-catalyst, such as quatern

Aluminium(salen) and tetrabutylammonium bromide catalysed synthesis of cyclic di- and trithiocarbonates from epoxides and carbon disulfide

The combination of a bimetallic aluminium(salen) complex and tetrabutylammonium bromide was found to catalyse the synthesis of cyclic di- and trithiocarbonates from epoxides and carbon disulfide. Reactions carried out at 50 °C produced 1,3-oxathiolane-2-thiones, whilst at 90 °C, 1,3-dithiolane-2-thiones were formed. Georg Thieme Verlag Stuttgart.

A bimetallic aluminum(salen) complex for the synthesis of 1,3-oxathiolane-2-thiones and 1,3-dithiolane-2-thiones

Figure presented. The combined use of the bimetallic aluminum(salen) complex [Al(salen)]2O and tetrabutylammonium bromide (or tributylamine) is found to catalyze the reaction between epoxides and carbon disulfide. In most cases, at 50 °C, the reaction produces 1,3-oxathiolane-2-thiones, while at 90 °C, 1,3-dithiolane-2-thiones are the main product. The structure and stereochemistry of three of the 1,3-dithiolane-2-thiones is unambiguously determined by X-ray crystallographic analysis, and this is used to correct errors in the literature concerning the synthesis of cyclic di- and trithiocarbonates. The kinetics of 1,3-oxathiolane-2-thione synthesis are determined, and the resulting rate equation, along with a stereochemical analysis of the reaction and catalyst modification studies, is used to determine a mechanism for the synthesis of 1,3-oxathiolane-2-thiones which contrasts with the mechanism previously determined for cyclic carbonate synthesis using the same bimetallic aluminum(salen) complex.

A simple and novel eco-friendly process for the synthesis of cyclic dithiocarbonates from epoxides and carbon disulfide in water

The reaction of oxiranes with carbon disulfide for preparation of cyclic dithiocarbonates was carried out in water under catalytic amount of an organic base such as dimethylaminopyridine or triethylamine. The reaction conditions are simple and give high y