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- W2093192086 abstract "The monofluorination by subtitution of the hydroxyl group of the β-hy-droxyesters of (o,m,p)ZC6H4C(OH)RCR′R″CO2R″′ structure (where Z = halogens, methyl, methoxy, nitro and H and R,R′,R″,R″,H or alkyl) and 2,2,2-trichloroaryléthanols by the phenyltetrafluorophosphorane according to the following synthetic route is described. The temperature θo at which the intermediate alkoxyphosphorane is decomposed determines the nature (alkene, alkoxytrifluorophosphorane, monofluorinated compounds) of the products and their yield. Knowlege of this temperature θo of erythro and threo isomers permits the selective fluorination of one of them in a mixture. Moreover, the action of the PhPF4 with four couples of the isoleted pur diastereoisomers of the β-hydroxyesters C6H5CHOHCHRCO2CH3 shows the stereoselectivity of the reaction. The structure of the isomeric 2-alkyl 3-fluoro 3-phenyl proprionates has been determined unabiguously by 1H and 19F NMR analysis. The mecanisms of the reaction which leads to the products summerized in the table are discussed." @default.
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- W2093192086 date "1980-12-01" @default.
- W2093192086 modified "2023-09-24" @default.
- W2093192086 title "Quantitative and stereoselective monofluorination of β-hydroxyesters by PhPF4" @default.
- W2093192086 doi "https://doi.org/10.1016/s0022-1139(00)84074-9" @default.
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