3278-38-4Relevant articles and documents
Synthesis and antimicrobial properties of esters of 2-alkyl-3-aryl-2-(O-alkyl-dithiocarbonato)propionic acid
Grishchuk,Vlasik,Blinder,Gorbovoi,Kudrik
, p. 711 - 713 (1996)
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A Novel Method for the Direct Synthesis of Symmetrical and Unsymmetrical Sulfides and Disulfides from Aryl Halides and Ethyl Potassium Xanthogenate
Soleiman-Beigi,Arzehgar
, p. 986 - 992 (2018/02/09)
An efficient and new method for the synthesis of disulfides and sulfides via the reaction of aryl halides with ethyl potassium xanthogenate in the presence of MOF-199 is described. O -Ethyl- S -aryl carbonodithioate has a key role as an intermediate in this procedure; it was converted into symmetrical diaryl disulfides in DMF. Additionally, this could be applied to the synthesis of unsymmetrical aryl alkyl(aryl′) disulfides by the reaction with S -alkyl(aryl) sulfurothioates (Bunte salts) as well as unsymmetrical aryl alkyl(aryl′) sulfides in DMSO.
Synthesis of unsymmetrical sulfides using ethyl potassium xanthogenate and recyclable copper catalyst under ligand-free conditions
Akkilagunta, Vijay Kumar,Kakulapati, Rama Rao
supporting information; experimental part, p. 6819 - 6824 (2011/10/09)
The synthesis of unsymmetrical sulfides has been achieved in good to excellent yields with inexpensive ethyl potassium xanthogenate via cross-coupling reaction using recyclable CuO nanoparticles under ligand-free conditions.The copper oxide nanoparticles can be recovered and reused up to five cycles without loss of activity.
Hydrolysis and aminolysis of alkyl xanthate esters and cellulose analogues
Humeres, Eduardo,Soldi, Valdir,Klug, Marilene,Nunes, Mauricea,Oliveira, Celia M.S.,Barrie, Patrick J.
, p. 1050 - 1056 (2007/10/03)
The hydrolysis and aminolysis of a series of S-substituted O-alkylxanthate esters was studied in 20% v/v aqueous methanol at 35°C. The pH-rate profiles of the hydrolyses showed water and hydroxide-ion-catalyzed reactions. The reaction of 2,4-dinitrophenyl cellulose xanthate (CelXDNP) and p-nitrobenzyl cellulose xanthate (CelXNB) with polyalanine and lysozyme produced a covalent bond between the polypeptide and the cellulose matrix, as shown by solid-state 13C NMR. However, the nature of the bonding could not be identified. The reaction of nucleophiles (H2O, OH-, RNH2) and xanthic esters was consistent with an addition-elimination mechanism through a tetrahedral intermediate. Bronsted plots against the pKa of the nucleophile (βnu) or the nucleofuge of the substrate (βlg) were used to characterize the rate-determining step. The pKa values of the nucleophiles ranged between -1.74 and 15.74, and for the nucleofuges, they were in the range of 10.50-0.92. For nucleophiles with pKa values up to about 10, βlg was 0.10-0.15, and βnu changed from 0.48 to 0.35 for the strongest electron-withdrawing nucleofuge. It was concluded that the water-catalyzed hydrolyses, and also aminolyses with moderately basic amines, occur with rate-determining formation of the tetrahedral intermediate. For strong bases such as hydroxide ion, the disappearance of the intermediate becomes the slowest step. The reaction of cellulose xanthic esters with external nucleophiles as hydroxide ion and amines shows simple first-order kinetics and is slower than alkyl or sugar xanthates, probably due to the diffusion effect through the tight cybotactic region of cellulose.
