13679-60-2Relevant articles and documents
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.
