75717-38-3Relevant academic research and scientific papers
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.
ON THE USE OF beta PHENYLSULFINYL- alpha , beta -UNSATURATED CARBONYL DIENEOPHILES IN DIELS-ALDER REACTIONS.
Danishefsky,Harayama,Singh
, p. 7008 - 7012 (2007/10/10)
The use of beta -phenylsulfinyl- alpha , beta -unsaturted carbonyl dieneophiles as synthetic equivalents of alpha , beta -ethynyl carbonyl systems has been demonstrated. The sulfoxides were prepared by oxidation of the sulfides, which in turn were obtained from the beta -dicarbonyl systems by standard methods. A key feature of the scheme is that the phenylsulfinyl group does not compete with the carbonyl function in determining the regiochemistry of cycloaddition with the highly nucleophilic trans-1-methoxy-3-trimethylsilyloxy-1,3-butadiene. Application of the methodology to the synthesis of the disodium prephenate dimethyl acetals is described.
