111-31-9Relevant articles and documents
A practical, one-step synthesis of primary thiols under mild and neutral conditions using bis(triorganotin) sulfides
Gingras,Harpp
, p. 1397 - 1400 (1990)
Thiols are obtained from primary organic halides and bis(triaryl/alkyltin) sulfides in the presence of fluoride ion in CH3CN/H2O at 20°C. This simple one-step methodology involving fluorodestannylation is carried out under mild and neutral conditions, in sharp contrast to virtually all known methods. Some attempts at utilizing triorganotin and triorganogermanium mercaptans for the same purpose are reported.
Characterization of initial reaction intermediates in heated model systems of glucose, glutathione, and aliphatic aldehydes
Wang, Tianze,Zhen, Dawei,Tan, Jia,Xie, Jianchun,Cheng, Jie,Zhao, Jian
, (2019/09/12)
To understand the effect of lipid degradation on Maillard formation of meaty flavors, initial reaction intermediates in model systems of glucose–glutathione with hexanal, (E)-2-heptenal, or (E,E)-2,4-decadienal were identified by HPLC–MS and by NMR. Besides Amadori compounds, hemiacetals and thiazolidines via addition of sulfhydryl to carbonyl or to the conjugated olefinic bond were found. Concentrations of all intermediates increased with reaction time while degradation of the intermediates with a glutathione moiety helped formation of thiazolidines with cysteinylglycine. The unsaturated aldehydes (E)-2-heptenal and (E,E)-2,4-decadienal exhibited high reactivity against glucose for glutathione, yielding higher levels of intermediate compounds than from glucose. Heating prepared intermediates reversibly released the original aldehydes, which caused various compounds formed by retro-aldol, oxidation, etc. to react with H2S and NH3. Among them, formation pathways including 3-nonen-2-one, 2-hexanoylfuran, and six dialkylthiophenes (e.g., 2-ethyl-5-(1-methylbutyl)thiophene) were proposed for the first time.
Phosphorus pentasulfide mediated conversion of organic thiocyanates to thiols
Maurya, Chandra Kant,Mazumder, Avik,Gupta, Pradeep Kumar
supporting information, p. 1184 - 1188 (2017/07/03)
In this paper we report an efficient and mild procedure for the conversion of organic thiocyanates to thiols in the presence of phosphorus pentasulfide (P2S5) in refluxing toluene. The method avoids the use of expensive and hazardous transition metals and harsh reducing agents, as required by reported methods, and provides an attractive alternative to the existing methods for the conversion of organic thiocyanates to thiols.
A rhodium(i)-oxygen adduct as a selective catalyst for one-pot sequential alkyne dimerization-hydrothiolation tandem reactions
Kleinhans, George,Guisado-Barrios, Gregorio,Liles, David C.,Bertrand, Guy,Bezuidenhout, Daniela I.
supporting information, p. 3504 - 3507 (2016/03/04)
An air-stable rhodium(i)-oxygen adduct featuring a CNC-pincer ligand, based on 1,2,3-triazol-5-ylidenes, catalyzes the homo-dimerization and hydrothiolation of alkynes, affording the gem-enyne and α-vinyl sulfide isomers, respectively, with excellent selectivity. A one-pot stepwise strategy allows the selective catalytic preparation of non-symmetric bis-vinyl sulfides, as well as the alkyne dimerization-hydrothiolation tandem reactions.