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

RD Chambers, M Parsons, G Sandford, E Thomas…

Index: Chambers, Richard D.; Parsons, Mandy; Sandford, Graham; Thomas, Emmanuelle; Trmcic, Jelena; Moilliet, John S. Tetrahedron, 2006 , vol. 62, # 30 p. 7162 - 7167

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Citation Number: 9

Abstract

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 ...