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Mechanistic Investigation of Superelectrophilic Activation of 1,1′-bi-2-Naphthols in the Presence of Aluminum Halides Full article

Journal Organic and Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539
Output data Year: 2019, Volume: 17, Number: 16, Pages: 3971-3977 Pages count : 7 DOI: 10.1039/c9ob00640k
Tags IONIC HYDROGENATION; BINOL; CYCLOHEXANE; ACID; NAPHTHALENEDIOLS; CONDENSATION; BENZENE
Authors Zhu Zhongwei 1 , Genaev Alexander M. 2 , Salnikov George E. 1,2,3 , Koltunov Konstantin Yu. 1,4
Affiliations
1 Novosibirsk State University, Pirogova 2, Novosibirsk 630090, Russia
2 Vorozhtsov Novosibirsk Institute of Organic Chemistry, Pr. Lavrentieva 9, Novosibirsk, Russia
3 International Tomography Center, Institutskaya 3a, Novosibirsk, Russia
4 Boreskov Institute of Catalysis, Pr. Lavrentieva 5, Novosibirsk, Russia

Funding (1)

1 Russian Foundation for Basic Research 17-03-00564 (АААА-А17-117040310053-5)

Abstract: 7,7′-Dihydroxy-1,1′-bi-2-naphthol, as a result of superelectrophilic activation in the presence of an excess of aluminum halides, reacts with cyclohexane and benzene to yield 5,6,7,8,5′,6′,7′,8′-octahydro-7,7′-dioxo-bi-2-naphthol and its 5,5′-diphenyl derivative, respectively. In contrast, isomeric 6,6′-dihydroxy-1,1′-bi-2-naphthol does not react at all under the same reaction conditions, while the parent 1,1′-bi-2-naphthol (BINOL) reveals an alternative mode of behavior. The mechanistic aspects of these intriguing results are discussed on the basis of experimental and theoretical (DFT) study of the protonation and complexation properties of the starting BINOLs.
Cite: Zhu Z. , Genaev A.M. , Salnikov G.E. , Koltunov K.Y.
Mechanistic Investigation of Superelectrophilic Activation of 1,1′-bi-2-Naphthols in the Presence of Aluminum Halides
Organic and Biomolecular Chemistry. 2019. V.17. N16. P.3971-3977. DOI: 10.1039/c9ob00640k WOS Scopus РИНЦ AN OpenAlex
Dates:
Submitted: Mar 19, 2019
Accepted: Mar 25, 2019
Published online: Mar 27, 2019
Published print: Apr 28, 2019
Identifiers:
Web of science: WOS:000466500800010
Scopus: 2-s2.0-85064695674
Elibrary: 38675000
Chemical Abstracts: 2019:627810
OpenAlex: W2924789713
Citing:
DB Citing
Scopus 2
Web of science 2
Elibrary 1
OpenAlex 2
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