37054-53-8Relevant academic research and scientific papers
Gold-Catalyzed Oxidation of Thioalkynes to Form Phenylthio Ketene Derivatives via a Noncarbene Route
Sharma, Pankaj,Singh, Rahulkumar Rajmani,Giri, Sovan Sundar,Chen, Liang-Yu,Cheng, Mu-Jeng,Liu, Rai-Shung
, p. 5475 - 5479 (2019/08/01)
Gold-catalyzed oxidations of thioalkynes with 8-methylquinoline oxides afford 2-phenylthioketenes that can be trapped efficiently with alcohols. The synthetic utility is manifested by terminal and internal thioalkynes over a wide scope, bearing esters, ke
KI-catalyzed C-S bond formation: Via an oxidation relay strategy: Efficient access to various α-thio-β-dicarbonyl compounds
Jiang, Yi,Zou, Jiao-Xia,Huang, Long-Tao,Peng, Xue,Deng, Jie-Dan,Zhu, Long-Qing,Yang, Yu-Hang,Feng, Yi-Yue,Zhang, Xiao-Yun,Wang, Zhen
supporting information, p. 1641 - 1645 (2018/03/21)
An efficient and practical methodology to obtain α-thio-β-dicarbonyl compounds was presented under alkaline conditions via potassium iodide (KI) catalysis; various symmetrical/unsymmetrical 1,3-dicarbonyl compounds were obtained under an aerobic atmospher
Pyrolysis of (2-Phenylethyl)phenylsulfonium Ylides
Yoshimura, Toshiaki,Motoyama, Atsushi,Morishige, Akiko,Tsukurimichi, Eiichi,Shimasaki, Choichiro,Hasegawa, Kiyoshi
, p. 174 - 180 (2007/10/02)
In order to obtain information concerning the reaction mechanism of the pyrolysis of sulfonium ylides bearing a substituted phenyl group on the 2-position in the S-ethyl group of ethylphenylsulfonium ylide, (2-phenylethyl)phenylsulfonium bis(methoxycarbonyl)methylide (1) and dicyanomethylide(2) were subjected to pyrolysis in benzene.The reaction rates of 1 and 2 at 140 deg C were 6.0- and 3.2-times faster than those of ethylphenylsulfonium bis(methoxycarbonyl)methylide and dicyanomethylide, respectively.The activation parameters for 1 were ΔH++=125 kJ mol-1 and ΔS++=-3.8 JK-18mol-1, while those for 2 were ΔH++=124 kJ mol-1 and ΔS++=-2.5 JK-1 mol-1.Substituent efects on the β-phenyl groups in 1 and 2 afforded positive Hammett ρ-values: ρ = 0.49 (γ = 0.997) and ρ = 0.26 (γ = 0.993), respectively.From the obtained results, it was suggested that the pyrolysis proceeds through essentially a concerted intramolecular cis-elimination inclined toward a slightly carbanion-like type from an E1-like type by introducing a phenyl substituent at the 2-position of the ethyl group in the ethylphenylsulfonium ylide.
Alkylation of Position C-5 of Triacetic Acid Lactone by Sigmatropic Rearrangement of Sulphonium Ylides
March, Pedro de,Moreno-Manas, Marcial,Ripoll, Isabel
, p. 1413 - 1420 (2007/10/02)
Reactions of the 4-methoxy-6-(phenylthiomethyl)-2H-pyran-2-ones 4 with three different diazo compounds under copper or rhodium catalysis give the corresponding sulphonium ylides, which through sigmatropic rearrangement and further prototropy afford the pyrones 6, functionalized at the difficultly accessible position C-5.Desulphurations of products 6 with deactivated Raney nickel give the pyrones 17-19.The influence of the experimental conditions on the competition between sigmatropic and Stevens rearrangement has been studied for the reaction of 4-methoxy-6-(phenylthiomethyl)-2H-pyran-2-one (4a) and dimethyl diazomalonate.Several products (9, 10, and 11) arising from sulphonium ylides equilibration and radical recombination have been found in addition to the sigmatropic and the Stevens rearrangement products 6d and 8.
