Synthesis of Thioesters by Simultaneous Activation of Carboxylic Acids and Alcohols Using PPh₃/NBS with Benzyltriethylammonium Tetrathiomolybdate as the Sulfur Transfer Reagent

Abstract

A new and simple route for the synthesis of thioesters starting from carboxylic acids and alcohols is reported by using tetrathiomolybdate as the key sulfur transfer reagent. Triphenylphosphane and N-bromosuccinimide were used for the activation of the carboxylic acid and alcohol in the same pot followed by the transfer of sulfur from tetrathiomolybdate. Thioesters were obtained in good to moderate yields. Pri-

Alternative Protocol for the Synthesis of Symmetrical Dibenzyl Diselenides and Disulfides

“…30 In another example, when a mixture of benzoic acid and benzyl alcohol was treated with Ph 3 P/NBS followed by the tetrathiomolybdate, benzyl alcohol preferentially reacted to form dibenzyl disulfide instead of the thioester of benzoic acid. 31 Inspired by the results obtained with the diselenides, we envisaged in situ activation of benzyl alcohols by the VR followed by treatment with sulfurated borohydride, 32 NaBH 2 S 3 , as a sulfur-transfer reagent to obtain the corresponding disulfides. NaBH 2 S 3 can be readily synthesized using NaBH 4 and elemental sulfur, and is generally employed for the reduction of aldehydes, oximes, ketones, and nitro, nitrile, amide and nitroso compounds.…”

Oxygen, sulfur, selenium, tellurium and polonium

“…The synthesis of thio-esters has been achieved by reaction of alcohols and carboxylic acids with MoS 4 2À as the source of S. 137 Thioamides and selenoamides have been prepared by direct reaction of the parent amide with elemental chalcogen in the presence of hydrochlorosilanes (eg. HSiCl 3 ) and an amine base.…”

Solubility of Benzyl Disulfide in Five Organic Solvents between (283.45 and 333.15) K

“…According to the study, we choose five organic solvents (ethanol, n -hexane, ethyl acetate, toluene, and chloroform) to measure the solubilities of benzyl disulfide, which are practical in crystallization process and have never been reported previously. The five organic solvents have different polarities and are widely used in producing benzyl disulfide in organic synthesis. − Moreover, the measurements of the solid–liquid equilibrium and the foundation of thermodynamic models are crucial in the study. The Apelblat equation, Buchowski (λ h ) equation, NRTL equation, Hansen equation, and Wilson equation are usually used to study the solubilities of solids. , The modified Apelblat equation is selected to be the equation which correlates the experimental data.…”