Mechanistic Investigation of Superelectrophilic Activation of 1,1′-bi-2-Naphthols in the Presence of Aluminum Halides | Sciact - CRIS-система Института катализа

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

Ключевые слова

IONIC HYDROGENATION; BINOL; CYCLOHEXANE; ACID; NAPHTHALENEDIOLS; CONDENSATION; BENZENE

Авторы

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

Организации

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

Информация о финансировании (1)

Российский фонд фундаментальных исследований

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 CAPlus OpenAlex

Поступила в редакцию:	19 мар. 2019 г.
Принята к публикации:	25 мар. 2019 г.
Опубликована online:	27 мар. 2019 г.
Опубликована в печати:	28 апр. 2019 г.

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

БД	Цитирований
Scopus	2
Web of science	2
РИНЦ	1
OpenAlex	2