Mechanistic Investigation of Superelectrophilic Activation of 1,1′-bi-2-Naphthols in the Presence of Aluminum Halides | Sciact - CRIS-system of Boreskov Institute of Catalysis

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)

Russian Foundation for Basic Research

17-03-00564 (АААА-А17-117040310053-5)

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.

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

Submitted:	Mar 19, 2019
Accepted:	Mar 25, 2019
Published online:	Mar 27, 2019
Published print:	Apr 28, 2019

Web of science:	WOS:000466500800010
Scopus:	2-s2.0-85064695674
Elibrary:	38675000
Chemical Abstracts:	2019:627810
OpenAlex:	W2924789713

DB	Citing
Scopus	2
Web of science	2
Elibrary	1
OpenAlex	2