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Protonation Behavior of 1,1'-Bi-2-naphthol and Insights into Its Acid-Catalyzed Atropisomerization.

Organic Letters 2017 Februrary 4
The behavior of 1,1'-bi-2-naphthol (BINOL) in variety of (super)acid media has been studied by NMR. The results are combined with the theoretical (DFT) study of the role of mono- and diprotonated forms of BINOL in the acid-catalyzed atropisomerization of this compound. It is demonstrated that the process of enantiomeric configuration exchange proceeds mainly via internal rotation around the C1(sp3 )-C1'(sp3 ) bond in intermediates such as C1-monoprotonated keto or C1,C1'-diprotonated forms of BINOL, depending on the acidity level.

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