Reactions of 2,3-Naphthalenediol with Cyclohexane in the Presence of Aluminum Halides | Sciact - CRIS-system of Boreskov Institute of Catalysis

Reactions of 2,3-Naphthalenediol with Cyclohexane in the Presence of Aluminum Halides Full article

Journal

Tetrahedron Letters
ISSN: 0040-4039

Output data

Year: 2015, Volume: 56, Number: 17, Pages: 2254-2257 Pages count : 4 DOI: 10.1016/j.tetlet.2015.03.059

Tags

Ionic hydrogenation, Naphthols, Superacids, Superelectrophiles

Authors

Zhu Zhongwei ^1,2 , Ostashevskaya Ludmila A. ¹ , Koltunov Konstantin Yu. ^1,3

Affiliations

1	Novosibirsk State University, Pirogova, 2, Novosibirsk 630090, Russia
2	Heilongjiang University, Xue Fu Road, No. 74, Nan-gang, Harbin 150080, PR China
3	Boreskov Institute of Catalysis, Siberian Branch of the Russian Academy of Sciences, Pr. Akademika Lavrentieva, 5, Novosibirsk 630090, Russia

2,3-Naphthalenediol (7) undergoes selective ionic hydrogenation with cyclohexane in the presence of excess AlCl3 or AlBr3 to afford 5,6,7,8-tetrahydro-2,3-naphthalenediol (8). Compound 8 can be further converted into 5,6,7,8-tetrahydro-1,2-naphthalenediol (9) and pyrocatechol (10). The discovered reactions represent new and efficient synthetic approaches to produce difficult to obtain derivatives of 7. The mechanistic aspects of the reactions, and the potential involvement of superelectrophilic dicationic intermediates, are discussed.

Zhu Z. , Ostashevskaya L.A. , Koltunov K.Y.
Reactions of 2,3-Naphthalenediol with Cyclohexane in the Presence of Aluminum Halides
Tetrahedron Letters. 2015. V.56. N17. P.2254-2257. DOI: 10.1016/j.tetlet.2015.03.059 WOS Scopus РИНЦ ANCAN OpenAlex

Submitted:	Jan 28, 2015
Accepted:	Mar 13, 2015
Published online:	Mar 19, 2015
Published print:	Apr 1, 2015

Web of science:	WOS:000353745900031
Scopus:	2-s2.0-84937763215
Elibrary:	23992199
Chemical Abstracts:	2015:511011
Chemical Abstracts (print):	162:514135
OpenAlex:	W1963850969

DB	Citing
Web of science	7
Scopus	7
Elibrary	7
OpenAlex	7