77102-69-3

Upstream product

• 75-15-0 carbon disulfide 
• 75-03-6 ethyl iodide 
• 108-98-5 thiophenol 
• 74-96-4 ethyl bromide 
• 16911-89-0 phenyl chlorodithioformate 
• 75-08-1 ethanethiol 
• 1483-72-3 diphenyliodonium chloride 
• 35444-20-3 potassium ethyltrithiocarbonate 

Downstream Products

• 352-93-2 diethyl sulphide 
• 35994-88-8 tetrakis(ethylthio)ethene 
• 622-38-8 Ethyl phenyl sulfide 
• 74-85-1 ethene 
• 108-98-5 thiophenol 

Relevant academic research and scientific papers

Triethylamine-catalyzed one-pot synthesis of trithiocarbonates from carbon disulfide, thiols, and alkyl halides in water

Symmetrical and unsymmetrical trithiocarbonates were prepared by a simple and efficient one-pot reaction of thiols, carbon disulfide, and alkyl halides in the presence of triethylamine in water at room temperature.

Organic reactions in ionic liquids: Synthesis of alkyl aryl trithiocarbonates by the S-arylation of potassium carbonotrithioates with diaryliodonium salts

Various alkyl aryl trithiocarbonates were readily prepared in good yields by the S-arylation of potassium carbonotrithioates with diaryliodonium salts in the room-temperature ionic liquid, 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim]BF4). The ionic liquid can be recycled and reused.

The Mechanism of Thermal Eliminations. Part 24. Elimination from Mono-, Di-, and Trithiocarbonates. The Dependence of the Transition State Polarity, Thione to Thiol Rearrangement, and Ether Formation via Nucleophilic Substitution, on Compound Type.

We have measured rates of thermal decomposition and Arrhenius parameters for S-alkyl O-phenyl thiocarbonates, O-alkyl O'-phenyl thiocarbonates, S-alkyl O-phenyl and O-alkyl S-phenyl dithiocarbonates (xanthates), and alkyl phenyl trithiocarbonates between 671.4 and 819.2 deg K.The reactivity order is: PhOCSOR>PhOCO2R>PhSCSOR>PhSCO2R>PhOCSSR>PhSCSSR>PhOCOSR>(PhSCOSR).Compared with the pyrolysis of acetates the rate decrease accompanying change of carbonyl to thiocarbonyl is smaller, whilst that accompanying change of OR to SR is greater, because the transition state for carbonate pyrolysis is more E1-like within the overall semi-concerted process.The accelerating effect of thion sulphur is greatest for ethyl derivatives which have the least E1-like transition state.The iPr/Et rate ratios at 700 deg K are: 30.7 (PhOCO2R), α-X bond breaking may be the most important rate determining step.Compounds containing thione sulphur and O-alkyl groups (but not O-phenyl groups) undergo sulphur-oxygen exchange.A mechanism for this exchange is given which accounts both for these structural aspects and the much slower exchange in thionacetates.For carbonates, exchange is more severe for compounds which have the slowest competing elimination.Compounds PSCSSiPr, PhSCSSEt, PhOCSSEt, and PhOCOSEt each gave abnormally low activation energies (and low stoicheiometry) due to competing nucleophilic substitution which gives ethers.This reaction is predicted to be important also for compounds PhSCOSR.

ONE-POT SYNTHESIS OF ALKYL ARYL TRITHIOCARBONATES FROM BENZENETHIOLS, ALKYL HALIDES, AND CARBON DISULFIDE WITH A PHASE-TRANSFER CATALYST.

Various alkyl aryl trithiocarbonates may readily be synthesized in good yield at low temperatures such as 20 degree C by allowing trioctylmethylammonium chloride (phase-transfer catalyst) to catalyze reaction of benzenethiols and alkyl halides with carbon disulfide.

Synthesis and Dediazoniation of 2-Butyl- and 2,5-Dibutylbenzenediazonium Ions

2-Butylbenzenediazonium ion (1a) and 2,5-dibutylbenzenediazonium ion (1b) have been thermally decomposed in aqueous acid solution.In addition to the major product, the corresponding phenol, 5- and 6-membered ring products are formed (in a ratio of ca. 7:1) as well as products of elimination and substitution in the o-butyl group.The formation of the non-phenolic products is explained in terms of competing reactions of the initially formed aryl cations: cyclization by electrophilic atttack on the o-butyl group and 1,5-hydride ion transfer from the o-butyl group with concomitant elimination or reaction with the medium.Decompositions of 1a in the presence of copper(I) oxide, believed to generate aryl radicals, does not yield any measurable quantities of cyclized products, however.