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

Результат исследования: Научные публикации в периодических изданияхстатья

15 Цитирования (Scopus)

Аннотация

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.

Язык оригиналаанглийский
Страницы (с-по)532-535
Число страниц4
ЖурналOrganic Letters
Том19
Номер выпуска3
DOI
СостояниеОпубликовано - 3 фев 2017

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