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• W2110764056 startingPage "8939" @default.
• W2110764056 abstract "1,3,4,6-Tetraketones typically undergo keto-enol tautomerism forming bis-enols stabilized by intramolecular hydrogen bonding in two six-membered rings. However, 1,3,4,6-tetraketones derived from the terpene ketone camphor and norcamphor exist as isomers with two distinguishable modes of intramolecular hydrogen bonding, namely, the formation of six- or seven-membered rings. The structural requirements for this so far unknown behavior were investigated in detail by synthesis and comparison of structural analogues. Both isomers of such 1,3,4,6-tetraketones were fully characterized in solution and in the solid state. Intriguingly, they slowly interconvert in solution by means of tautomerism-rotation cascades, as was corroborated by DFT calculations. The influence of temperature and complexation with the transition metals Pd, Rh, and Ir on the interconversion process was investigated." @default.
• W2110764056 created "2016-06-24" @default.
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• W2110764056 date "2015-05-04" @default.
• W2110764056 modified "2023-10-16" @default.
• W2110764056 title "Tautomerization-Mediated Molecular Switching Between Six- and Seven-Membered Rings Stabilized by Hydrogen Bonding" @default.
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• W2110764056 doi "https://doi.org/10.1002/chem.201500524" @default.
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• W2110764056 hasPublicationYear "2015" @default.
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