1438-91-1Relevant articles and documents
A Facile One-pot Synthesis of Sulfides from Alkyl Halides and Alcohols Using Tetramethylthiourea
Fujisaki, Shizuo,Fujiwara, Isamu,Norisue, Yasumasa,Kajigaeshi, Shoji
, p. 2429 - 2430 (1985)
Sulfides can be readily prepared under mild conditions by a reaction of tetramethylthiourea with alkyl halides and alcohols in the presence of sodium hydride in satisfactory yields.The scope and limitation of this method are also presented.
Structure-Odor Correlations in Homologous Series of Mercapto Furans and Mercapto Thiophenes Synthesized by Changing the Structural Motifs of the Key Coffee Odorant Furan-2-ylmethanethiol
Schoenauer, Sebastian,Schieberle, Peter
, p. 4189 - 4199 (2018/05/01)
Furan-2-ylmethanethiol (2-furfurylthiol; 2-FFT, 1) is long-known as a key odorant in roast and ground coffee and was also previously identified in a wide range of thermally treated foods such as meat, bread, and roasted sesame seeds. Its unique coffee-like odor quality elicited at very low concentrations, and the fact that only a very few compounds showing a similar structure have previously been described in foods make 1 a suitable candidate for structure-odor activity studies. To gain insight into the structural features needed to evoke a coffee-like odor at low concentrations, 46 heterocyclic mercaptans and thio ethers were synthesized, 32 of them for the first time, and their odor qualities and odor thresholds were determined. A movement of the mercapto group to the 3-position kept the coffee-like aroma but led to an increase in odor threshold. A separation of the thiol group from the furan ring by an elongation of the carbon side chain caused a loss of the coffee-like odor and also led to an increase in odor thresholds, especially for ω-(furan-2-yl)alkane-1-thiols with six or seven carbon atoms in the side chain. A displacement of the furan ring by a thiophene ring had no significant influence on the odor properties of most of the compounds studied, but the newly synthesized longer-chain 1-(furan-2-yl)- and 1-(thiophene-2-yl)alkane-1-thiols elicited interesting passion fruit-like scents. In total, only 4 out of the 46 compounds also showed a coffee-like odor quality like 1, but none showed a lower odor threshold. Besides the odor attributes, also retention indices, mass spectra, and NMR data of the synthesized compounds were elaborated, which are helpful in possible future identification of these compounds in trace levels in foods or other materials.
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.
