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

Chambers, R.D.; Parsons, M.; Sandford, G.; Thomas, E.; Trmcic, J.; Moilliet, J.S.

Authors

R.D. Chambers

M. Parsons

G. Sandford

E. Thomas

J. Trmcic

J.S. Moilliet



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 substitution process, although mixtures of fluorinated products are obtained in most cases.

Citation

Chambers, R., Parsons, M., Sandford, G., Thomas, E., Trmcic, J., & Moilliet, J. (2006). Elemental fluorine. Part 19: Electrophilic fluorination of hexyl derivatives bearing electron withdrawing groups. Tetrahedron, 62(30), 7162-7167. https://doi.org/10.1016/j.tet.2006.03.113

Journal Article Type Article
Acceptance Date Mar 30, 2006
Online Publication Date May 11, 2006
Publication Date Jul 24, 2006
Deposit Date Apr 26, 2007
Journal Tetrahedron
Print ISSN 0040-4020
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 62
Issue 30
Pages 7162-7167
DOI https://doi.org/10.1016/j.tet.2006.03.113

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