1917-05-1Relevant academic research and scientific papers
Cyanuric chloride as promoter for the oxidation of sulfides and deoxygenation of sulfoxides
Bahrami, Kiumars,Khodaei, Mohammad M.,Sohrabnezhad, Samira
, p. 6420 - 6423 (2011)
This Letter discusses the use of cyanuric chloride as an efficient promoter for the chemoselective oxidation of sulfides to the corresponding sulfones in the presence of H2O2 as the terminal oxidant. Sulfoxides were also found to undergo deoxygenation to sulfides with cyanuric chloride and potassium iodide system. The reaction is broad in scope and easy to perform.
TAPC-catalyzed synthesis of thioethers from thiols and alcohols
Bahrami, Kiumars,Khodaei, Mohammad Mehdi,Khodadoustan, Nayere
experimental part, p. 2206 - 2210 (2011/10/09)
A new synthesis of thioethers is described. The reaction of aryl alcohols with aryl, heteroaryl, and alkyl thiols in the presence of TAPC as an efficient catalyst affords good to excellent yields of thioethers. Furthermore, the reaction proceeds under metal-free and solvent-free conditions thus represents an interesting complement to known methods for thioether synthesis. A plausible mechanism for this reaction is delineated. Georg Thieme Verlag Stuttgart · New York.
TAPC-promoted oxidation of sulfides and deoxygenation of sulfoxides
Bahrami, Kiumars,Khodaei, Mohammad M.,Sheikh Arabi, Mehdi
supporting information; experimental part, p. 6208 - 6213 (2010/11/04)
Figure presented. 1,3,5-Triazo-2,4,6-triphosphorine-2,2,4,4,6,6- tetrachloride (TAPC) was found to be an efficient promoter for the oxidation of sulfides and deoxygenation of sulfoxides. Excellent yields, short reaction time, easy and quick isolation of the products, solvent-free process, and excellent chemoselectivity are the main advantages of this procedure.
Simple synthesis of furfuryl sulfides via extrusion of COS from the xanthates and its mechanistic aspects
Eto, Masashi,Nishimoto, Mituhiro,Uemura, Toshihiro,Hisano, Takuzo,Harano, Kazunobu
, p. 1155 - 1162 (2007/10/02)
Heating of O-furfuryl S-alkyl dithiocarbonates (xanthates) gave furfuryl alkyl sulfides together with S-furfuryl S-alkyl dithiocarbonates.The crossover reaction using differently substituted furfuryl xanthates in polar solvents indicates that the reaction proceeds intermolecularly, whereas the reaction in non-polar solvents showed intramolecular reaction behaviour.The reaction is first-order and the rates are considerably affected by a change in the solvent polarity.The activation enthalpy and entropy for the extrusion of O-furfuryl S-methyl xanthate in xylene are 28.0 +/- 1.3 kcal mol-1 and -2 +/- 4 cal K-1 mol-1, respectively.Based on these findings together with the MO calculation data, the mechanism for the conversion reaction of furfuryl xanthates to furfuryl alkyl sulfides is discussed.
