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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

Реферат: 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.
Библиографическая ссылка: 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 OpenAlex
Идентификаторы БД:
Web of science: WOS:000466500800010
Scopus: 2-s2.0-85064695674
РИНЦ: 38675000
OpenAlex: W2924789713
Цитирование в БД:
БД Цитирований
Web of science 2
Scopus 2
РИНЦ 1
OpenAlex 2
Альметрики: