Elemental fluorine. Part 19: Electrophilic fluorination of hexyl derivatives bearing electron withdrawing groups

Reaction of a series of model hexyl derivatives of the form C₆H₁₃-X (X=Cl, Br, I, CO₂Me, COMe, CHO) with both elemental fluorine and Selectfluor™ was studied in order to assess the impact of electron withdrawing functional groups upon fluorination of an alkyl chain. Fluorination generally occurs at secondary sites, with a slight preference for those that are furthest removed from the electron withdrawing group, consistent with an electrophilic substitution process, although mixtures of fluorinated products are obtained in most cases.