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 Научная публикация

Журнал

Organic and Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539

Вых. Данные

Год: 2019, Том: 17, Номер: 16, Страницы: 3971-3977 Страниц : 7 DOI: 10.1039/c9ob00640k

Авторы

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

Организации

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

Web of science	WOS:000466500800010
Scopus	2-s2.0-85064695674
РИНЦ	38675000
OpenAlex	W2924789713