42467-05-0Relevant articles and documents
Magnetically recyclable silica-coated ferrite magnetite-K10montmorillonite nanocatalyst and its applications in O, N, and S-acylation reaction under solvent-free conditions
Kumar, Pushpendra,Patil, Shripad M.,Tandon, Nitin,Tandon, Runjhun
, p. 21291 - 21300 (2021/07/01)
Novel silica-coated ferrite nanoparticles supported with montmorillonite (K10) have been prepared successfully by using a simple impregnation method. Further, these nanoparticles were characterized by using different analytical methods like FT-IR, PXRD, EDS, and FE-SEM techniques. In addition, these nanoparticles have been explored for their catalytic activity for the O, N, and S-acylation reactions under solvent-free conditions which gave moderate to excellent yields in a much shorter reaction time. Moreover, these nanoparticles could easily be separated out from the reaction medium after the reaction completion by using an external magnetic field and have been re-used for 10 cycles without any significant loss of the catalytic activity.
Thioesters as Bifunctional Reagents for 2-Naphthylamine Sulfuracylation
Xiao, Fuhong,Yuan, Shanshan,Wang, Dahan,Liu, Saiwen,Huang, Huawen,Deng, Guo-Jun
supporting information, p. 3331 - 3336 (2019/06/13)
An efficient and convenient strategy for the preparation of diaryl sulfides via a Fe-promoted direct sulfuracylation of 2-naphthylamine using thioesters as bifunctional reagents is described. This synthetic strategy features high chemoselectivity, good substrate scope and functional group tolerance. (Figure presented.).
Fungicidal Activity of S-Esters of Thiocarboxylic Acids as Antimicrobial Additives to Petroleum Products
Aliev,Belovezhets,Oparina
, p. 99 - 105 (2019/04/27)
Abstract: A variety of aliphatic and aromatic S-esters of thiocarboxylic acids have been tested for antimicrobial activity. The relationship between the chemical structure of the compounds R1SC(O)R2 and their toxicity for microorganisms has been revealed, and the effect of various functional groups on the antimicrobial properties has been shown. The cooling lubricant IKhP-45E with S-aryl thioacetate additives has been tested. It has been shown that the additives used (0.25–0.5 wt %) inhibit the growth of all the studied microorganisms; however, their activity with respect to fungi is higher. The introduction of S-aryl thioacetates provides the resistance of these oils to microbiological deterioration to retain the physicochemical properties for a long period of time.
S-Acetylation of Thiols Mediated by Triflic Acid: A Novel Route to Thioesters
Kuciński, Krzysztof,Hreczycho, Grzegorz
, p. 489 - 493 (2018/04/27)
This paper demonstrates an efficient, mild, and chemoselective synthesis of various thioesters via a HOTf-catalyzed S-acetylation of aromatic and aliphatic thiols using isopropenyl acetate as a cheap and convenient acetylating agent. During our tests, we also investigated the differences between the activities of metal triflates and triflic acid as catalysts in the acetylation of thiols. Finally, the potential of our concept has been increased by the implementation of Nafion as a heterogeneous catalyst for S-acetylation of thiols.
Rapid and convenient synthesis of S-acetylarenethiols by non-aqueous diazotization
Liu, Rui,Li, Yu-Hao,Chang, Jin,Xiao, Qi,Zhu, Hong-Jun
experimental part, p. 3059 - 3064 (2010/11/04)
A series of S-acetylarenethiols were synthesized from aromatic amines by a rapid, convenient and efficient method. Arenediazonium tetrafluoroborates were afforded from aromatic amines, isoamyl nitrite and boron trifluoride etherate in non-aqueous diazotization system, then reacted with potassium thioacetate in dimethylsulfoxide to obtain desired products in moderate to good yields and short reaction times. The product S-acetyl-4-iodothiophenol was characterized by single crystal X-ray diffraction. The crystal belongs to monoclinic, space group P21/C with unit cell parameters: a = 0.594 20(12) nm, b = 0.542 00(11) nm, c = 2.9618(6) nm, α = 90.00°, β = 94.23(3)°, γ = 90.00°, Dx = 1.942 g/cm3, Z = 4, F(000) = 528, μ = 3.528 mm-1, R = 0.039 2, wR = 0.099 3, P = (Fo2 + 2Fc2)/3, S = 1.077, (Δρ)max = 0.692 x 1030 e/m3, (Δρ)min = -0.558 x 1030 e/m3. The X-ray crystallographic structure (CCDC-684683) clearly shows that the para atoms I and S lie in the benzene ring plane and no hydrogen bonds were observed.
Mimicry of polyketide synthases - Enantioselective 1,4-addition reactions of malonic acid half-thioesters to nitroolefins
Lubkoll, Jana,Wennemers, Helma
, p. 6841 - 6844 (2008/09/17)
Bifunctionality is the key for mimicking the active site of polyketide synthases with synthetic metal-free organocatalysts (see picture). Cinchona alkaloid derivatives bearing both a basic site and a urea moiety catalyze conjugate enantioselective addition reactions of malonic acid half thioesters (MAHTs) to nitroolefins with up to quantitative yields and selectivities up to 90% ee. (Chemical Equation Presented).
1H, 13C and 17O NMR study of substituent effects in 4-substituted phenylthiol esters
Perumal, Subbu,Vasuki, Gnanasambandam,Vijayabaskar, Veerappan,Selvaraj, Sangavanaicker,Boykin, David W.
, p. 720 - 726 (2007/10/03)
The 1H and 13C NMR spectra of 4-substituted phenylthiol acetates, benzoates and cinnamates and the 17O NMR spectra of a few thiol acetates were measured. The 13C chemical shifts of C-1 of the thiol esters when correlated with appropriate substituent-induced chemical shifts (SCS) of monosubstituted benzenes reveal an enhancement of substituent effect at C-1. Several good dual substituent parameter (DSP) correlations of 13C chemical shifts with σ1 and σR parameters were obtained for the carbons para to the substituent and the carbonyl carbons of all the three series of thiol esters display inverse substituent effects, indicating π-polarization of the thiol ester functionality by the dipole of the substituent. John Wiley & Sons Ltd.
Photooxygenation of vinyl sulfides: Substituent effects on the [2+2] cycloaddition versus Schenck ene reaction modes
Adam, Waldemar,Sampath Kumar,Saha-Moeller, Chantu R.
, p. 7853 - 7854 (2007/10/02)
Electron-accepting substituents at the para position of aryl vinyl sulfides 1 promote the ene reaction with singlet oxygen in competition with the usual [2+2] cycloaddition, while electron-donating substituents afford exclusively dioxetane product, which through their thermally labile nature decompose by C-C cleavage to the corresponding carbonyl fragments.
