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

Ponce Gonzalez, J, Edgar, M, Elsegood, MRJ and Weaver, GW (2011) Synthesis of fluorinated fused benzofurans and benzothiophenes: Smiles-type rearrangement and cyclisation of perfluoro(het)aryl ethers and sulfides Org. Biomol. Chem., 9. 2294-2305 - 2294-2305.

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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.

Item Type: Article
Authors :
NameEmailORCID
Ponce Gonzalez, JUNSPECIFIEDUNSPECIFIED
Edgar, MUNSPECIFIEDUNSPECIFIED
Elsegood, MRJUNSPECIFIEDUNSPECIFIED
Weaver, GWUNSPECIFIEDUNSPECIFIED
Date : 2011
Identification Number : 10.1039/C0OB00790K
Related URLs :
Depositing User : Symplectic Elements
Date Deposited : 17 May 2017 13:33
Last Modified : 17 May 2017 13:33
URI: http://epubs.surrey.ac.uk/id/eprint/839659

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