Reinvestigation of the substituent effects of fluorine on the 1 H NMR chemical shifts of the adjacent methylene group in fluorinated [2.2]paracyclophanes

Abstract Introduction of a fluorine substituent into an aromatic ring of [2.2]paracyclophane causes distinct shielding and deshielding effects at the anti ‐ and syn ‐protons, respectively, of the adjacent bridge methylene group. A recent contradictory claim in the literature was disproved by 2D H,H‐NOESY, long‐range H,H‐COSY and H,C‐HMBC experiments. Copyright © 1999 John Wiley & Sons, Ltd.