Intramolecular versus intermolecular oxidative couplings of ester tethered di-aryl ethers

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Journal Article
Tetrahedron, 2007, 63 (46), pp. 11377 - 11385
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The oxidative cyclization of 3,4-dimethoxyphenyl 3,4-dimethoxyphenylacetate, through intramolecular biphenyl bond formation, was successful and gave the target seven-membered lactone in good yield (8586%). All other ester substrates gave biphenyl products or their further oxidized products via intermolecular coupling of their radical cation intermediate with the neutral substrate. It appears that matching of the oxidation potentials and nucleophilicity of the two phenyl rings, the positioning of the ring substituents and the ease of E to Z isomerization about the ester CO bond are important factors contributing to these product outcomes.
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