77111-62-7Relevant academic research and scientific papers
Triethylamine-catalyzed one-pot synthesis of trithiocarbonates from carbon disulfide, thiols, and alkyl halides in water
Movassagh, Barahman,Soleiman-Beigi, Mohammad
experimental part, p. 927 - 930 (2009/09/06)
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.
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.
Al-Awadi, Nouria,Taylor, Roger
, p. 177 - 182 (2007/10/02)
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.
Sugawara,Shirahata,Sato,Sato
, p. 3353 - 3354 (2007/10/02)
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.
