33944-98-8Relevant academic research and scientific papers
Reaction of Arynes with Vinyl Sulfoxides: Highly Stereospecific Synthesis of ortho-Sulfinylaryl Vinyl Ethers
Li, Yuanming,Studer, Armido
supporting information, p. 666 - 669 (2017/02/10)
The reaction of in situ generated arynes with aryl vinyl sulfoxides provides ortho-arylsulfinylaryl vinyl ethers via aryne σ-bond insertion into the S-O-bond and concomitant stereospecific S-O-vinyl migration. The cascade allows preparing di- or trisubsti
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
Production method of optically active trans-vinylsulfide alcohol
-
, (2008/06/13)
PCT No. PCT/JP96/03185 Sec. 371 Date Jun. 30, 1997 Sec. 102(e) Date Jun. 30, 1997 PCT Filed Oct. 30, 1996 PCT Pub. No. WO97/16421 PCT Pub. Date May 9, 1997A method for producing an optically active trans-vinylsulfide alcohol having the formula: wherein R1 represents an alkyl group or an aryl group, comprising the step of reducing a trans-vinylsulfide ketone with a borane reducing agent in the presence of an optically active oxazaborolidine and an additive.
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
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.
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
Sulfinyl-controlled Formation of Diastereoisomerically Pure Tricarbonyl(oxadiene)iron(0) Complexes and a Diastereoisomerically Pure Tetracarbonyl(alkene)iron(0) Complex
Ibbotson, Arthur,Reis, Ana C. Reduto dos,Saberi, Stephen P.,Slawin, Alexandra M. Z.,Thomas, Susan E.,et al.
, p. 1251 - 1260 (2007/10/02)
The sulfonyl and sulfinyl substituted oxadienes nCH=CHC(Me)=O; R=But, Ph; n = 2,1> form stable tricarbonyliron(0) complexes.The sulfinyl complexes formed are diastereoisomerically pure and the relative stereochemistry of the tricarbonyliron(0) unit and the sulfinyl substituent in the products has been determined by an X-ray crystal structure analysis of 0tS(O)CH=CHC(Me)=O>(CO)3> 15a.Phenylsulfonylethene and phenylsulfinylethene form stable tetracarbonyliron(0) complexes.The complex formed from phenylsulfinylethene is diastereoisomerically pure and the relative stereochemistry of the tetracarbonyliron(0) unit and the sulfinyl substituent has been determined by an X-ray crystal structure analysis of 0(CO)4> 18.This reveals evidence for a through-space interaction between the oxygen atom of the sulfinyl substituent and the carbon atom of one of the metal carbonyl ligands.The X-ray crystal structure analysis of 17, a by-product in the formation of complex 18, is also reported.
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.
