Abstract
Abstract α-Oxyradicals generated from alcohols and ethers underwent addition to the vinyl sulfone 3-fluoro-2,3-dihydro-1H-λ6-thiophene-1,1-dione (1) giving a new family of fluorinated compounds. The stereochemistry of the addition products 3–8 was confirmed by using both 19 F NMR spectroscopy and X-ray crystallography. In all cases, trans-isomers were preferentially formed. The π-facial stereoselection fails to follow the hyperconjugative theory of Cieplak, instead other possible explanations have been proposed underlying the importance of electronic contributions to the observed diastereoselectivity. An additional vinyl sulfone 2-bromo-4-fluoro-4,5-dihydro-1H-λ6-thiophene-1,1-dione (10) was prepared via the successive bromination and dehydobromination of 1; its addition reaction with 2-propanol was also studied.
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