Pentafluorostyrene reacts with sodium methoxide, methylamine, dimethylamine, and lithium anilide with replacement of the fluorine para to the vinyl group only. It is concluded that significant replacement by nucleophiles of fluorine ortho to a substituent X in C6F5X requires that X be of the type Y![[double bond, length half m-dash]](https://www.rsc.org/images/entities/char_e006.gif)
Z, that is, dipolar and unsaturated.
J. Burdon and W. T. Westwood, J. Chem. Soc. C, 1970, 1271 DOI: 10.1039/J39700001271
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