Mechanistic investigation of superelectrophilic activation of 1,1 '-bi-2-naphthols in the presence of aluminum halides

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

Authors

Zhu Zhongwei ¹ , Genaev Alexander M. ² , Salnikov George E. ^1,2,3 , Koltunov Konstantin Yu. ^1,4

Affiliations

1	(Данные Web of science) Novosibirsk State Univ, Pirogova 2, Novosibirsk 630090, Russia
2	(Данные Web of science) Vorozhtsov Novosibirsk Inst Organ Chem, Pr Lavrentieva 9, Novosibirsk 630090, Russia
3	(Данные Web of science) Int Tomog Ctr, Inst Skaya 3a, Novosibirsk 630090, Russia
4	(Данные Web of science) Boreskov Inst Catalysis, Pr Lavrentieva 5, Novosibirsk 630090, Russia

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

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