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Novel reaction of allylic alcohols with a hexafluoropropene-diethylamine adduct (PPDA) to form α-fluoro-α-(trifluoromethyl)-γ,δ-unsaturated amides

✍ Scribed by Ken-ichi Ogu; Motohiro Akazome; Katsuyuki Ogura

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
235 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

Since fluorinated orsenic compounds are well known to usually show unique chemical, physical, and bioioskal properties, l-3 various methods have been developed for introducing fluorine atom(s) into orsmic molecules. Althoushthefluoro(trifluommahyl)methylenemoiety (A) is one ofthe most intrisuinsfluorlne-contsini~ fonetionalities, there have appeered only a few papers relevant to this moiety, which utilize some derivatives of 2,3,3,3-tetrafluoropropanoic acid. 4"6 Furthennore~ a hexafluoropropene-diethylamine edduct (PPDA) was reported to produce 2,3,3,3-telrafluoroproponic esters in the reaction with some alcohols. 7 Recently, we discovered a stereoapeeific formmion of ¢x-

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Stereoselective formation of α-fluoro-α-
Stereoselective formation of α-fluoro-α-trifluoromethyl-γ-lactones starting from γ-hydroxy-α,β-unsaturated sulfones and a hexafluoropropene-diethylamine adduct (PPDA)
✍ Katsuyuki Ogura; Ken-ichi Ogu; Takashi Ayabe; Jun-ichi Sonehara; Motohiro Akazom 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 205 KB

E)-3-Hydroxy-l-dkenyl p-tolyl sulianes (1) reacted with a hexaluoropropene-.diethylamine adduet (PPDA) to aflbrd ct-fluora-ct-(trilluoromethyi)-l~-[(p-tulylsullanyl)methyl].ff-laetones (2). This reaction is so steteoselective that only one diastel'eomer of 2 is detected in the reaction mixttt~. A pl