Acid-Catalyzed Versus Thermally Induced C1–C1′ Bond Cleavage in 1,1′-Bi-2-naphthol: An Experimental and Theoretical Study | Sciact - CRIS-система Института катализа

Acid-Catalyzed Versus Thermally Induced C1–C1′ Bond Cleavage in 1,1′-Bi-2-naphthol: An Experimental and Theoretical Study Научная публикация

Журнал

Journal of Organic Chemistry
ISSN: 0022-3263 , E-ISSN: 1520-6904

Вых. Данные

Год: 2019, Том: 84, Номер: 11, Страницы: 7238-7243 Страниц : 6 DOI: 10.1021/acs.joc.9b00915

Ключевые слова

Chemistry; Organic compounds

Авторы

Genaev Alexander M. ¹ , Shchegoleva Lyudmila N. ¹ , Salnikov George E. ^1,2,3 , Shernyukov Andrey V. ^1,2 , Shundrin Leonid A. ^1,2 , Shundrina Inna K. ^1,2 , Zhu Zhongwei ² , Koltunov Konstantin Yu. ^2,4

Организации

1	N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Pr. Akademika Lavrentieva 9, Novosibirsk 630090, Russia
2	Novosibirsk State University, Pirogova 2, Novosibirsk 630090, Russia
3	International Tomography Center, Institutskaya 3a, Novosibirsk 630090, Russia
4	Boreskov Institute of Catalysis, Pr. Akademika Lavrentieva 5, Novosibirsk 630090, Russia

Информация о финансировании (1)

Российский фонд фундаментальных исследований

17-03-00564 (АААА-А17-117040310053-5)

Experiments show that 1,1′-bi-2-naphthol (BINOL) undergoes facile C1–C1′ bond cleavage under action of triflic acid at temperatures above 0 °C to give mainly 2-naphthol along with oligomeric material. CASSCF and MRMP//CASSCF computations have demonstrated unambiguously that this unusual mode of scission of the biaryl bond can occur in the C1,C1′-diprotonated form of BINOL via a mechanism involving homolytic cleavage prompted by the intramolecular electrostatic repulsion. These findings also provide insights into the mechanism of a comparatively easy thermal cleavage of BINOL, implying the intermediacy of its neutral diketo form.

Genaev A.M. , Shchegoleva L.N. , Salnikov G.E. , Shernyukov A.V. , Shundrin L.A. , Shundrina I.K. , Zhu Z. , Koltunov K.Y.
Acid-Catalyzed Versus Thermally Induced C1–C1′ Bond Cleavage in 1,1′-Bi-2-naphthol: An Experimental and Theoretical Study
Journal of Organic Chemistry. 2019. V.84. N11. P.7238-7243. DOI: 10.1021/acs.joc.9b00915 WOS Scopus РИНЦ CAPlus PMID OpenAlex

Поступила в редакцию:	3 апр. 2019 г.
Опубликована online:	14 мая 2019 г.
Опубликована в печати:	7 июн. 2019 г.

Web of science:	WOS:000471212000063
Scopus:	2-s2.0-85066959293
РИНЦ:	41647947
Chemical Abstracts:	2019:936838
PMID (PubMed):	31083942
OpenAlex:	W2946321888

БД	Цитирований
Scopus	10
Web of science	8
РИНЦ	7
OpenAlex	10