An Unexpected Reversal of Fluorine Substituent Effects in the Biomethylenation of Two Positional Isomers: A Serendipitous Discovery

Article abstract of DOI:10.1021/jo00313a004

The mechanism of biological cyclopropyl fatty acid biosynthesis as it occurs in Lactobacillus plantarum has been probed using fluorine substituent effects.It has been shown that the pattern of rate retardations induced by homoallylic fluorine substitution is numerically the same but opposite in sense for two series of olefinic fatty acid substrates bearing the double bond at either the 9- or the 11-position.