Abstract:
Compared with the parent 1,1’-bi-2-naphthol (BINOL), its dimethyl ether is highly resistant towards racemization under moderate acidic conditions. This finding confirms the hypothetical mechanism of BINOL atropisomerization including internal rotation around the C1sp3 –C1'sp3 bond in its protonatedforms.
Citation:
A. M. Genaev, G. E. Salnikov, A. V. Shernyukov, Zh. Zhu, K. Yu. Koltunov, “Enhanced enantiostability of BINOL dimethyl ether under moderate acidic conditions”, Mendeleev Commun., 28:1 (2018), 27–28
Linking options:
https://www.mathnet.ru/eng/mendc1651
https://www.mathnet.ru/eng/mendc/v28/i1/p27
This publication is cited in the following 5 articles:
“SYNTHESIS OF AROMATIC ACETYLENE ALCOHOLS USING COMPLEX CATALYTIC SYSTEMS”, CHEMISTRY AND CHEMICAL ENGINEERING, 2021, 58
Barbara Wisser, Andreas Labahn, Christian Näther, Christoph Janiak, “Supramolecular Ammine‐Copper rac‐BINOLAT Salts through in‐situ R‐ or S‐BINOL Racemization”, Zeitschrift anorg allge chemie, 646:13 (2020), 734
K. Intaraboonrod, T. Lerdwiriyanupap, M. Hoquante, G. Coquerel, A. E. Flood, “Temperature cycle induced deracemization”, Mendeleev Commun., 30:4 (2020), 395–405
Alexander M. Genaev, Lyudmila N. Shchegoleva, George E. Salnikov, Andrey V. Shernyukov, Leonid A. Shundrin, Inna K. Shundrina, Zhongwei Zhu, Konstantin Yu. Koltunov, “Acid-Catalyzed Versus Thermally Induced C1–C1′ Bond Cleavage in 1,1′-Bi-2-naphthol: An Experimental and Theoretical Study”, J. Org. Chem., 84:11 (2019), 7238
G. E. Salnikov, A. M. Genaev, A. V. Shernyukov, Z. Zhu, N. V. Tkachenko, K. Yu. Koltunov, “Configurational Stability of 1,1′-Bi-2-naphthol in Superacid System HSO3F–SbF5–SO2ClF”, Russ J Org Chem, 54:5 (2018), 792
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