1452261-49-2Relevant academic research and scientific papers
On the selectivity of silver mediated thiolate transfer and the crystal structure of an unprecedented thiolate chloride Argentate(I) anion
Moreno-Alcántar, Guillermo,Romo-Islas, Guillermo,Flores-álamo, Marcos,Torrens, Hugo
, p. 149 - 153 (2018)
The reactivity of a series of fluorinated silver(I) thiolates (AgSRF) towards thiolation of dichloromethane by nucleophilic substitution in presence of bis(diphenylphosphane)methane (dppm) has been studied. Our results indicate that in the presence of an excess of CH2Cl2 the thiolate phosphine silver derivatives are capable of exchange thiolate and chloride to form, in different proportions, the correspondent chloromethylthioether (CH2Cl(SRF)) a or methyldithioether (CH2(SRF)2) b with the fluorinated SRF groups: SC6F4H 1, SC6H4(CF3)-2 2, SC6H3F2-3,4 3, SC6H3F2-2,4 4, SC6H3F2-3,5 5 and SC6H4F-2 6. Despite the kinetically preferred monosubstitution reaction, some of the thiolate derivatives tend to form selectively the disubstitution products, indicating a non-innocent role of the silver center in the formation of the product. Furthermore, we have isolated and structurally characterized, by X-ray diffraction, an ionic compound [Ag3(μ3-Cl)2(μ-Ph2PCH2PPh2)3][AgCl(SC6F4H)] that could be an intermediary product in the chloride-thiolate exchange reactions.
Sc(OTf)3-Catalyzed Synthesis of Symmetrical Dithioacetals and Bisarylmethanes Using Nitromethane as a Methylene Source
Dethe, Dattatraya H.,Shukla, Manmohan,Dherange, Balu D.
supporting information, p. 5778 - 5782 (2020/07/30)
Use of nitromethane as an electrophilic methylene source for the synthesis of symmetrical dithioacetals and bisarylmethanes has been showcased using Sc(OTf)3 as a catalyst. The procedure allows straightforward access to the densely functionalized dithioacetals and bisarylmethanes under mild conditions. Additionally, the method has been applied for the synthesis of antimalarial tetramethyl mellotojaponin C and anticancer dimeric phloroglucinol derivative.
A one-pot stereoselective synthesis of electron-deficient 4-substituted (E, E)-1-arylsulfonylbuta-1,3-dienes and their chemoselective [3+2] cycloaddition with azomethine ylides - A simple synthesis of 1,3,4-trisubstituted pyrrolidines and pyrroles
Sankar, Ulaganathan,Mahalakshmi, Susarla,Balasubramanian, Kalapattukuppuswamy
supporting information, p. 1533 - 1540 (2013/08/23)
A simple and efficient method for the synthesis of (E,E)-1-(arylsulfonyl) buta-1,3-dienes bearing electron-withdrawing substituents like cyano and ethoxycarbonyl at position 4, involving a one-pot alkylation of bis(phenylsulfonyl)methane with trans-ethyl 4-bromocrotonate/trans-4- bromocrotononitrile, and elimination of arylsulfinic acid, is described. These dienes undergo facile mono [3+2] cycloaddition with azomethine ylides chemoselectivity to furnish functionalized 1,3,4-trisubstituted pyrrolidines. Oxidation of these cycloadduct with MnO2·SiO2 under mild conditions provides 1,3,4-trisubstituted pyrroles. Georg Thieme Verlag Stuttgart. New York.
