59790-38-4Relevant academic research and scientific papers
Generation of Nonstabilized Thiazolium and 2-Methylthiazolium Methylides
Tsuge, Otohiko,Kanemasa, Shuji,Kuraoka, Satoru
, p. 1570 - 1573 (1985)
Desilylation of 3-(trimethylsilylmethyl)thiazolium triflates including 2-methyl derivatives with CsF generates the corresponding thiazolium methylides which are trapped with acetylenic and olefinic dipolarophiles.This paper presents the first example for the generation of nonstabilized thiazolium methylides including 2-methyl derivatives.
Sulfonium Ylides by (3+2) Cycloaddition of Arynes with Vinyl Sulfides: Stereoselective Synthesis of Highly Substituted Alkenes
Li, Yuanming,Mück-Lichtenfeld, Christian,Studer, Armido
supporting information, p. 14435 - 14438 (2016/11/11)
The reaction of in situ generated arynes with vinyl sulfides provides benzannulated sulfonium ylides in a (3+2) cycloaddition. Trapping of the intermediate ylides with electrophiles (proton transfer or a second aryne addition) and subsequent β-elimination give rise to di-, tri-, or tetrasubstituted alkenes with high stereoselectivity. Experimental studies and DFT calculations provide insight into the mechanisms of these cascade reactions.
Direct benzothiophene formation via oxygen-triggered intermolecular cyclization of thiophenols and alkynes assisted by manganese/PhCOOH
Liu, Kaisheng,Jia, Fan,Xi, Hui,Li, Yuanming,Zheng, Xiaojian,Guo, Qiaoxia,Shen, Baojian,Li, Zhiping
, p. 2026 - 2029 (2013/06/04)
An intermolecular oxidative cyclization between thiophenols and alkynes for benzothiophene formation has been established. A variety of multifunctional benzothiophenes are synthesized. In addition, we demonstrated that the obtained benzothiophenes can be
A green and rapid approach for the stereoselective vinylation of phenol, thiol and amine derivatives in water
Sarrafi, Yaghoub,Sadatshahabi, Marzieh,Alimohammadi, Kamal,Tajbakhsh, Mahmood
supporting information; experimental part, p. 2851 - 2858 (2011/11/06)
The stereoselective formation of C-O, C-S and C-N bonds by the reaction of phenols, thiols and amines with activated alkynes is described. The reactions are successfully conducted in water with excellent yields at room temperature. The lack of organic sol
Water-promoted regioselective hydrothiolation of alkynes
Bhadra, Sukalyan,Ranu, Brindaban C.
experimental part, p. 1605 - 1609 (2010/04/03)
Water promotes hydrothiolation of unactivated alkynes efficiently without any catalyst or additive. The reaction at room temperature furnishes vinyl sulfides with high regioselectivity via anti-Markovnikov addition. The terminal al- kynes provide dithiola
Soluble and polymer-supported 2- and 3-benzylated furans for the preparation of α,β-ethylenic carbonyl compounds
Albert, Sébastien,Soret, Adrien,Blanco, Luis,Deloisy, Sandrine
, p. 2888 - 2900 (2007/10/03)
Soluble and polymer-supported 2- and 3-benzylated furans were subjected to a sequence involving a Diels-Alder reaction with α,β-acetylenic carbonyl compounds, a Michael addition, and a subsequent retro-Diels-Alder reaction to yield olefinic compounds. On solid support, this traceless strategy is advantageous since pure compounds were released in the thermal cycloreversion step. The fur-2-ylated resin allowed a highly diastereoselective synthesis.
Reaction of Benzenesulphenyl Chloride with α, β-Unsaturated Compounds: Part I - Reactions with Methyl Crotonate and Methyl Cinnamate in Presence of Pyridine
Bhongle, N. N.,Gogte, V. N.,Vankar, Y. D.
, p. 724 - 728 (2007/10/02)
Reaction of benzenesulphenyl chloride (PhSCl) with α, β-unsaturated systems, in the presence of pyridine, offers a convenient route to sulphenylate regiospecifically the α-position of such systems.The specific role of pyridine and the product analysis have been examined and rationalised on the basis of the formation of pyridine-assisted carbanion intermediates and the structure/stability of these carbanions.
New Unusually Photochemical Reactions of 3-Aminosydnones
Gotthardt, Hans,Reiter, Friedemann
, p. 1737 - 1745 (2007/10/02)
The light-induced reactions of the 3-amino-4-(phenylthio)sydnones 1a - d surprisingly produce beside diphenyl disulfide the sydnone isomers 11a - d with 2-aza-1,3-diazoniacyclopentadiene-1,4-diolate structure in 2,3 - 27percent yields.The photoreactions of the sydnones 1a, c in the presence of dimethyl acetylenedicarboxylate proceed with formation of the photoisomers 11a or 11c (17percent), the benzothiophene derivative 14 (9 - 7percent), the (phenylthio)fumaric ester 15 (5percent) as well as the pyrazole derivatives 13a (18percent) or 13c (8percent), respectively.The latter are results of a thermal cycloaddition reaction of the photochemically generated nitrile imine intermediate of type 9 to dimethyl acetylenedicarboxylate.Beside 14 (30 - 43percent), the same pyrazole derivatives 13a, c are obtained on irradiation of the sydnone isomers 11a or 11c in the presence of dimethyl acetylenedicarboxylate, respectively.The analogous photoreaction of the system 1d/dimethyl acetylenedicarboxylate produces 11d (0.6percent) and 13d (1.8percent) in low yields.
Catalysis by molybdenum complexes. The reaction of diazenes and acetylenes with thiophenol
McDonald,Corbin,Newton
, p. 2056 - 2061 (2007/10/05)
The reaction of diethyl azodicarboxylate with thiophenol to give the appropriate hydrazine and disulfide is catalyzed by various oxomolybdenum compounds, Vaska's compound, and triethylamine. Of these same compounds, only OMo(S2CNR2)
