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Title: Synthesis of fluorinated fused benzofurans and benzothiophenes: smiles-type rearrangement and cyclisation of perfluoro(het)aryl ethers and sulfides
Authors: Gonzalez, Julia Ponce
Edgar, Mark
Elsegood, Mark R.J.
Weaver, George W.
Issue Date: 2011
Publisher: © The Royal Society of 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.
Abstract: 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.
Description: 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
Version: Accepted for publication
DOI: 10.1039/c0ob00790k
URI: https://dspace.lboro.ac.uk/2134/11881
Publisher Link: http://dx.doi.org/10.1039/c0ob00790k
ISSN: 1477-0520
Appears in Collections:Published Articles (Chemistry)

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