16900-08-6Relevant articles and documents
Aliphatic thioethers by s-alkylation of thiols via trialkyl borates
Gunes, Deniz,Sirkecioglu, Okan,Bicak, Niyazi
experimental part, p. 1685 - 1690 (2010/09/17)
A simple and convenient one-pot procedure is described for the synthesis of thioethers via boron esters. This procedure involves in-situ generation of alkyl sulfates by reaction of trialkyl borates with concentrated sulfuric acid and subsequent reaction with thiols in the presence of pyridine. The reactions with boron esters of primary or secondary alcohols proceed cleanly at 100C and afford aliphatic thioethers in reasonable yields (59-93%) within 24 h. Interestingly, the 1H NMR spectra of the products showed no sign of positional isomerisms. The method fails however with thiophenol and does not yield aromatic thioethers, due to electrophilic substitution at the phenyl ring. Copyright Taylor & Francis Group, LLC.
Et3B Induced Radical Addition of Thiols to Acetylenes
Ichinose, Yoshifumi,Wakamatsu, Kuni,Nozaki, Kyoko,Birbaum, Jean-Luc,Oshima,Koichiro,Utimoto, Kiitiro
, p. 1647 - 1650 (2007/10/02)
Thiols added easily to acetylenic compounds in the presence of Et3B to give alkenyl sulfides in good yields.The reaction of acetylenes with 3-methyl-2-buten-1-thiol gave dihydrothiophene derivatives in one pot.
Gas-Liquid Phase-transfer Synthesis of Phenyl Ethers and Sulphides with Carbonate as Base and Carbowax as Catalyst
Angeletti, Enrico,Tundo, Pietro,Venturello, Paolo
, p. 1137 - 1142 (2007/10/02)
When a mixture of a phenol (or thiol) and an alkyl halide is passed, in the gaseous state, through a solid bed of potassium carbonate (or sodium hydrogencarbonate) and catalytic amounts of Carbowax 6000, contained in a glass column at 170 deg C, the corresponding ethers (or sulphides) may be collected at the outlet.The Carbowax acts in a similar manner to the crown ethers used in solid-liquid phase-transfer catalysis.The potassium carbonate-Carbowax combination allows the generation of anions up to pKa of ca. 12.The catalysis mechanism is discussed and the synthesis of several ethers and thioethers is reported, some of which are obtained only with difficulty by normal liquid-liquid phase-transfer catalysis.