108644-07-1Relevant academic research and scientific papers
Regio- and Stereoselective Hydrosulfonylation of Electron-Deficient Alkynes: Access to Both E- and Z-β-Sulfonyl-α,β-Unsaturated Carbonyl Compounds
Zhang, Wei,Johnson, Gabriel M.,Guan, Zhi,He, Yan-Hong
supporting information, p. 4562 - 4570 (2018/10/24)
A metal-free hydrosulfonylation of electron-deficient alkynes with sodium sulfinates or sulfinic acids to access both E- and Z-β-sulfonyl-α,β-unsaturated carbonyl compounds has been developed. We propose that this reaction via a hydroxylallene intermediate delivers the thermodynamically stable E isomer, or via a concerted termolecular AdE3 mechanism affords Z isomer. The stereoselectivity of addition (syn or anti) can be controlled by varying the sulfonyl sources and acidic buffer solutions. This protocol exhibits broad substrate scope for internal or terminal alkynes including various substituted ynones and alkynyl esters. This approach is mild, efficient, operationally simple and easy to be scaled-up. (Figure presented.).
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.
