Journal
JOURNAL OF FLUORINE CHEMISTRY
Volume 128, Issue 5, Pages 540-544Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2007.01.006
Keywords
4-pentenamide; fluorine-containing halide; Na2S2O4; free radical addition; gamma-butyrolactones with fluorinated side chain
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The free radical additions of fluorine-containing halides to 4-pentenamides initiated by Na2S2O4 were investigated. Both polyfluoroalkyl iodide and ethyl iododifluoroacetate, gave rise to fluorine-containing gamma-butyrolactones as the main products while bromides such as ethyl bromodi-fluoroacetate 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 gamma-butyrolactones with fluorinated side chains. (C) 2007 Elsevier B.V. All rights reserved.
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