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Synthesis of fluorinated fused benzofurans and benzothiophenes: smiles-type rearrangement and cyclisation of perfluoro(het)aryl ethers and sulfides

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posted on 2013-03-07, 11:13 authored by Julia Ponce Gonzalez, Mark Edgar, Mark ElsegoodMark Elsegood, George WeaverGeorge Weaver
Lithium–bromine exchange in 2-bromophenyl perfluoroaryl ethers or sulfides affords fused fluorinated benzofurans or benzothiophenes respectively by SNAr substitution of the adjacent fluorine in the perfluoroaryl substituent. The structures of the new compounds were confirmed by NMR spectroscopy and single crystal X-ray diffraction analysis. In the case of 2-bromophenyl tetrafluoropyrid-4-yl ether, lithiation promoted a Smiles-type rearrangement which led to formation of 4-(2-hydroxyphenyl)tetrafluoropyridine, for which the structure was confirmed by X-ray crystallography.

History

School

  • Science

Department

  • Chemistry

Citation

GONZALEZ, J.P. ... et al., 2011. Synthesis of fluorinated fused benzofurans and benzothiophenes: smiles-type rearrangement and cyclisation of perfluoro(het)aryl ethers and sulfides. Organic and Biomolecular Chemistry, 9 (7), pp. 2294 - 2305.

Publisher

© The Royal Society of Chemistry

Version

  • AM (Accepted Manuscript)

Publication date

2011

Notes

This article was published in the journal, Organic and Biomolecular Chemistry [© Royal Society of Chemistry] and the definitive version is available at: http://dx.doi.org/10.1039/C0OB00790K

ISSN

1477-0520

Language

  • en

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