758-16-7Relevant articles and documents
Amide (A)–thioamide (T) interconversions using Ph3SiSH (A to T) and Ph3SnOH (T to A) reagents
Arias-Ugarte, Renzo N,Sharma, Hemant K,Pannell, Keith H
, p. 510 - 513 (2016/07/16)
Ph3SiSH transforms amides to thioamides and Ph3SnOH performs the reverse process, with the concomitant formation of Ph3SiOH (or Ph3SiOSiPh3) and Ph3SnSSnPh3, respectively. The chemistry is a delightful illustration of the oxophilicity of silicon compared to the thiophilicity of tin and occurs under relatively mild conditions, and for amide to thioamide transformation requires no amide activation. The chemistry is in accord with available data for Si?(S)(O), Sn?(O)(S) and C?(O)(S) bond energies. Copyright
Copper(I)-mediated direct trifluoromethylthiolation of allylic halides with elemental sulfur and (trifluoromethyl)trimethylsilane
Li, Jue,Wang, Peiqiang,Xie, Fei-Fei,Yang, Xi-Gang,Song, Xiao-Nan,Chen, Wei-Dong,Ren, Jiangmeng,Zeng, Bu-Bing
supporting information, p. 3568 - 3571 (2015/06/08)
Abstract A new method has been developed for the copper-mediated trifluoromethylthiolation of allylic halides by using potassium fluoride, elemental sulfur, and (trifluoromethyl)trimethylsilane in anhydrous N,N-dimethylformamide. This protocol provides facile access to a variety of allylic trifluoromethyl thioethers in moderate to good yields under mild, ligand-free reaction conditions.
Chromatographic component of identification of the transformation products of 1,1-dimethylhydrazine in the presence of sulfur
Zenkevich,Ul'Yanov,Golub,Buryak
, p. 1106 - 1114 (2014/08/05)
The gas-chromatographic retention indices of the products of 1,1-dimethylhydrazine transformations in the presence of sulfur allows one to confirm and, in ceratin cases, make more exact the results of their gas chromatography-mass spectrometry identificat
Metal-free oxidative trifluoromethylthiolation of terminal alkynes with CF3SiMe3 and elemental sulfur
Chen, Chao,Chu, Lingling,Qing, Feng-Ling
supporting information; experimental part, p. 12454 - 12457 (2012/09/05)
A metal-free oxidative trifluoromethyl-thiolation of terminal alkynes using readily available CF3SiMe3 and elemental sulfur at room temperature has been developed. This reaction provides an efficient and convenient method for the preparation of alkynyl trifluoromethyl sulfides bearing a wide range of functional groups. Preliminary investigation revealed that elemental sulfur instead of air acted as the oxidant.
In situ formation of thermally stable, room-temperature ionic liquids from CS2 and amidine/amine mixtures
Yu, Tao,Yamada, Taisuke,Weiss, Richard G.
scheme or table, p. 5492 - 5499 (2011/12/14)
Amidinium dithiocarbamates salts with diverse structures are prepared in situ by adding one equivalent of CS2 to an equimolar mixture of two nonionic molecules, an amidine and an amine. Many of the salts made in this way are room temperature ionic liquids (RTILs) and the others (ILs) melt well below the decomposition temperature of the salts, ca. 80 °C. Unlike the analogous amidinium carbamate RTILs, which are made by adding CO2 to amidine/amine mixtures and decompose near 50 °C, the amidinium dithiocarbamates do not revert to their amidine/amine mixtures when they are heated. The thermal, rheological, conductance, and spectroscopic properties of representative examples from a total of 50 of these ILs and RTILs are reported, comparisons between them and their nonionic phases (as well as with their amidinium carbamates analogues) are made, and the thermolysis pathways of the ammonium dithiocarbamates are investigated.
Direct thionation and selenation of amides using elemental sulfur and selenium and hydrochlorosilanes in the presence of amines
Shibahara, Fumitoshi,Sugiura, Rie,Murai, Toshiaki
supporting information; experimental part, p. 3064 - 3067 (2009/12/05)
Reactions of amides with elemental sulfur in the presence of hydrochlorosilanes and amines give the corresponding thioamides in good to high yields. The process takes place via reduction of elemental sulfur by the hydrochlorosilane in the presence of a suitable amine. The methodology can be applied to the selenation of amides by using elemental selenium. Thlonation and selenation of an acetyl-protected sialic acid derivative are found to take place selectively at the amide group.
Expeditious microwave-assisted thionation with the system PSCl 3/H2O/Et3N under solvent-free condition
Pathak, Uma,Pandey, Lokesh Kumar,Tank, Rekha
, p. 2890 - 2893 (2008/09/19)
(Chemical Equation Presented) A novel thionation protocol for carbonyl compounds, with the system PSCl3/H2O/Et3N has been discovered. Clean, rapid, and efficient synthesis of a variety of thiocarbonyl compounds such as thioamides, thiolactams, thioketones, thioxanthones, and thioacridone can be achieved through this simple and convenient method under solventless condition with microwave irradiation.
Dichlorothiophosphoric acid and dichlorothiophosphate anion as thionating agents in the synthesis of thioamides
Bezgubenko,Pipko,Sinitsa
experimental part, p. 1341 - 1344 (2009/02/07)
A method for the thionation of carboxylic acid amides with dichlorothiophosphoric acid and dichlorothiophosphate anion, providing thioamides in high yields, was developed. The facility of the thionation and the yields of the final products were shown to depend on the nature of the starting amide. The optimal reaction conditions are reported.
Dichlorophosphate anion in the synthesis of thioamides
Pipko,Simurova,Shvadchak,Bezgubenko,Luk'yanenko
, p. 1019 - 1021 (2008/02/05)
Phosphorus thiochloride reaction with dimethylformamide and dimethylacetamide leading to corresponding thioamides is studied. The thionylating agent is dichlorothiophosphate anion generated in the reaction course. Pleiades Publishing, Inc., 2006.
