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Reactions of dibromotetrafluorobenzene derivatives with sodium phenoxide salts. Competing hydrodebromination and SNAr processes |
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| Authors: | Benjamin Banks Graham Sandford Andrzej J Tadeusiak Dmitrii S Yufit Pinar Kilickiran |
| Institution: | a Department of Chemistry, Durham University, South Road, Durham DH1 3LE, UK b Chemical Crystallography Group, Department of Chemistry, Durham University, South Road, Durham DH1 3LE, UK c Sony Deutschland GmbH, Stuttgart Technology Center, Hedelfinger Strasse 61, 70327 Stuttgart, Germany |
| Abstract: | 1,2- and 1,3-dibromotetrafluorobenzene react with sodium phenoxide derivatives at sites para to ring bromine because these positions are activated by fluorine atoms ortho and meta to the site of nucleophilic substitution. Fluorine para to the site of nucleophilic attack is usually deactivating in nucleophilic aromatic substitution processes and this is reflected in the significantly reduced reactivity of 1,4-dibromotetrafluorobenzene which undergoes competing hydrodebromination processes to afford, primarily, 3-bromo-1,2,4,5-tetrafluorobenzene. |
| Keywords: | Nucleophilic aromatic substitution Perfluoroaromatic Dibromotetrafluorobenzene Bromophilic substitution Diaryl ether |
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