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Stereoselective formation of α-fluoro-α-trifluoromethyl-γ-lactones starting from γ-hydroxy-α,β-unsaturated sulfones and a hexafluoropropene-diethylamine adduct (PPDA)

✍ Scribed by Katsuyuki Ogura; Ken-ichi Ogu; Takashi Ayabe; Jun-ichi Sonehara; Motohiro Akazome

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
205 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

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 plausible mechanism for this intriguing reaction is discussed.

📜 SIMILAR VOLUMES

Novel reaction of allylic alcohols with
Novel reaction of allylic alcohols with a hexafluoropropene-diethylamine adduct (PPDA) to form α-fluoro-α-(trifluoromethyl)-γ,δ-unsaturated amides
✍ Ken-ichi Ogu; Motohiro Akazome; Katsuyuki Ogura 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 235 KB

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 intrisuinsfluo