Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 19, Issue 52, Pages 17827-17835Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201301969
Keywords
acetals; aromatic substitution; biaryls; dioxepines; tethers
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Funding
- Deutsche Forschungsgemeinschaft through the Center for Functional Nanostructures (CFN) [C3.3]
- Alexander von Humboldt Foundation
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2,2'-Biphenols are a large and diverse group of compounds with exceptional properties both as ligands and bioactive agents. Traditional methods for their synthesis by oxidative dimerisation are often problematic and lead to mixtures of ortho- and para-connected regioisomers. To compound these issues, an intermolecular dimerisation strategy is often inappropriate for the synthesis of heterodimers. The acetal method' provides a solution for these problems: stepwise tethering of two monomeric phenols enables heterodimer synthesis, enforces ortho regioselectivity and allows relatively facile and selective intramolecular reactions to take place. The resulting dibenzo[1,3]dioxepines have been analysed by quantum chemical calculations to obtain information about the activation barrier for ring flip between the enantiomers. Hydrolytic removal of the dioxepine acetal unit revealed the 2,2-biphenol target.
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