Na 2S 2O 4 initiated free radical additions of polyfluoroalkyl halides to 4-pentenamides

Abstract

The free radical additions of fluorine-containing halides to 4-pentenamides initiated by Na 2S 2O 4 were investigated. Both polyfluoroalkyl iodide and ethyl iododifluoroacetate, gave rise to fluorine-containing γ-butyrolactones as the main products while bromides such as ethyl bromodifluoroacetate gave the addition–reduction product. After steric and stereo effects on reaction yields were studied using various substrates, it was concluded that the reactions of 4-pentenamides and polyfluoroalkyl iodides provide one alternative approach to prepare γ-butyrolactones with fluorinated side chains.