33944-97-7Relevant academic research and scientific papers
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.
Dynamic thiol exchange with β-sulfidor-α,β-unsaturated carbonyl compounds and dithianes
Joshi, Gururaj,Anslyn, Eric V.
supporting information, p. 4714 - 4717,4 (2012/12/12)
A reversible covalent bond exchange of thiols, β-sulfido-α, β-unsaturated carbonyls, and dithianes has been studied in DMSO and D 2O/DMSO mixtures. The equilibrium between thiols and β-sulfido-α,β-unsaturated carbonyls is obtained within a few hours, while the equilibration starting with the β-dithiane carbonyls and thiols requires a few days. This time scale makes the system ideal for utilization in dynamic combinatorial chemistry.
Practical synthesis and highly diastereoselective diels-alder reactions of 1-alkylthio-3-silyloxybutadienes
Holmes, Janice M.,Albert, Andrea L.,Gravel, Michel
scheme or table, p. 6406 - 6409 (2009/12/06)
(Chemical Equation Presented) An efficient acid-catalyzed method for the synthesis of vinylogous thioesters was developed. 1-Alkylthio-3- silyloxybutadienes were then produced in high yields from the corresponding vinylogous thioesters. These dienes were
Additions of nucleophiles to 3-oxo-2,3-dihydrothiophene 1,1-dioxides. Formation of vinyl sulfides, thioacetals and enaminones
Hofslokkcn, Nini Unn,Skattebol, Lars
, p. 3085 - 3088 (2007/10/03)
3-Oxo-2,3-dihydrothiophene 1,1-dioxide (la) was prepared by oxidation of the commercially available 3methoxythiophene with dimethyldioxirane. Some other substituted 3-methoxythiophene derivatives were oxidized as well. Although the yields of these reactio
Methyl β-(benzotriazol-1-yl)vinyl ketone: A new β-acetylvinyl cation equivalent
Katritzky, Alan R.,Blitzke, Torsten,Li, Jianqing
, p. 3773 - 3781 (2007/10/03)
A simple and efficient two-step approach to methyl β-(benzotriazol-1-yl)vinyl ketone 7 is described. The synthetic utility of compound 7 has been demonstrated by nucleophilic substitutions of the benzotriazolyl group with a range of nucleophiles. Thus, me
Michael additions to 3(2H)-thiophenone 1,1-dioxide
Hofslokken, Nini,Flock, Solveig,Skattebo, Lars
, p. 119 - 122 (2007/10/02)
The addition of thiols and amines to 3(2H)thiophenone 1,1-dioxide takes place with extrusion of sulfur dioxide, furnishing in high yields the corresponding vinyl sulfides and enamines. Addition of dithiols afforded the corresponding thioacetals. The rates of the Michael addition and the extrusion reaction are strongly influenced by the solvent employed. In ethanol, sulfur dioxide extrusion took place even at room temperature.
Regio- and Stereo-selective Synthesis of β-Sulphonyl-α,β-Unsaturated Carbonyl Compounds via an Iodosulphonylation-Dehydroiodination Raction
Najera, Carmen,Baldo, Beatriz,Yus, Miguel
, p. 1029 - 1032 (2007/10/02)
α,β-Unsaturated carbonyl compounds underwent regiospecific iodosulphonylation with toluene-p-sulphonyl iodide or sodium toluene-p-sulphinate and iodine to afford products (2), which were stereoselectively dehydroiodinated by triethylamine to give β-sulphonyl derivatives (3).The reactivity of compounds (3) as cationic β-acylvinyl equivalents, tested with amines or thiophenol, gave compounds (4) resulting from a displacement reaction.
The Preparation of Some β-Sulfonylacrylate Thioesters and β-Sulfonylvinyl Ketones
Haynes, Richard K.,Vonwiller, Simone C.,Stokes, John P.,Merlino, Louisa M.
, p. 881 - 895 (2007/10/02)
β-Sulfonylacrylate phenyl and t-butyl thioesters, and β-sulfonylvinyl ketones have been prepared by oxidation of the corresponding β-aryl- and β-alkyl-thio compounds.In one case the β-sulfonylvinyl ketone was obtained from an epoxy sulfone.The β-aryl- and β-alkyl-thio compounds were obtained by chlorination-dehydrochlorination of saturated precursors.The reactions of 3-(phenylthio)propionyl chloride with organocadmium and Grignard reagents were used to prepare some of the saturated precursors of the β-sulfonylvinyl ketones.
Oxidative Functionalization of the β-Carbon in α,β-Unsaturated Systems. Preparation of 3-Phenylthio Enones, Acrylates, and Other Vinyl Derivatives
Bakuzis, Peter,Bakuzis, Marinalva L. F.
, p. 235 - 239 (2007/10/02)
The β-carbon of α,β-unsaturated ketones, esters, lactones, and nitriles can be oxidatively functionalized in a regiospecific manner in a simple sequence of reactions.Michael addition of thiophenol followed by oxidation with N-chlorosuccinimide gives chloro sulfides that readily lose HCl to give 3-phenylthio enones, acrylates, and other vinyl derivatives.
