Reductive activation of arenes: XIII. Reaction with butyl bromide of anionic products formed by reduction of 9,10-dicyanoanthracene with potassium in liquid ammonia

Reductive activation of arenes: XIII. Reaction with butyl bromide of anionic products formed by reduction of 9,10-dicyanoanthracene with potassium in liquid ammonia Full article

Journal

Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393

Output data

Year: 2001, Volume: 37, Number: 1, Pages: 62-66 Pages count : 5 DOI: 10.1023/A:1012373300561

Authors

Vaganova T.A. ¹ , Pokrovskii L.M. ¹ , Shteingarts V.D. ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Div, Novosibirsk 630090, Russia

Reduction of 9,10-dicyanoanthracene with one equivalent of metallic potassium in liquid ammonia at -33 degreesC gives a product which almost does not react with butyl bromide. By contrast, the two-electron reduction product reacts with butyl bromide to form, depending on the reaction conditions and procedure for treatment of the reaction mixture, one of the three compounds: 10-butyl-9-cyanoanthracene, 10-butyl-10-cyano-9,1 0-dihydroanthracen-9-one, or 9,10-dibutyl-9, 10-dicyano-9, 10-dihydroanthracene. Relatively stable 10-butyl-9,10-dicyano-9,10-dihydro-9-anthryl anion was presumed to be a common precursor of these products.

Vaganova T.A. , Pokrovskii L.M. , Shteingarts V.D.
Reductive activation of arenes: XIII. Reaction with butyl bromide of anionic products formed by reduction of 9,10-dicyanoanthracene with potassium in liquid ammonia
Russian Journal of Organic Chemistry. 2001. V.37. N1. P.62-66. DOI: 10.1023/A:1012373300561 WOS Scopus РИНЦ

Web of science	WOS:000169937800014
Scopus	2-s2.0-0035533715
Elibrary	13377719
OpenAlex	W3001442756