Reductive activation of arenes: XVI. Anionic products from reduction of p-tolunitrile with sodium in liquid ammonia and their reaction with butyl bromide

Reductive activation of arenes: XVI. Anionic products from reduction of p-tolunitrile with sodium in liquid ammonia and their reaction with butyl bromide Full article

Journal

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

Output data

Year: 2003, Volume: 39, Number: 5, Pages: 680-685 Pages count : 6 DOI: 10.1023/A:1026009329198

Authors

Vaganova T.A' ¹ , Starokon' E.V. ² , Shteingarts V.D. ¹

Affiliations

1	Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, pr. Akademika Lavrent'eva 9, Novosibirsk, 630090, Russia
2	Novosibirsk State University, Novosibirsk, Russia

Study of oxidation, protonation, and alkylation of the products obtained by one- and two-electron reduction of p-tolunitrile with sodium in liquid ammonia showed that these products are, respectively, p-tolunitrile radical anion and 1-cyano-4-methyl-2,5-cyclohexadienyl anion. The latter is formed by protonation of p-tolunitrile dianion with ammonia. The two-electron reduction involves protonation of p-tolunitrile dianion with initial p-tolunitrile, which gives rise to 4-cyanobenzyl anion. The yield of the latter depends on the order of mixing of the reactants. The anionic reduction products react with butyl bromide to afford products corresponding to ipso alkylation with respect to the cyano group, 4-butyltoluene and 3-butyl-3-cyano-6-methyl-1,4-cyclohexadiene, as well as the alkylation product at the benzylic position, 4-pentylbenzonitrile. The formation of 4-butyltoluene indicates the possibility for selective synthesis of p-alkyltoluenes by reductive alkylation of p-tolunitrile.

Vaganova T.A. , Starokon' E.V. , Shteingarts V.D.
Reductive activation of arenes: XVI. Anionic products from reduction of p-tolunitrile with sodium in liquid ammonia and their reaction with butyl bromide
Russian Journal of Organic Chemistry. 2003. V.39. N5. P.680-685. DOI: 10.1023/A:1026009329198 WOS Scopus РИНЦ

Ваганова Т.А. , Староконь Е.В. , Штейнгарц В.Д.
Восстановительная активация аренов xvi. анионные продукты восстановления п - тол унитрила натрием в жидком аммиаке и их взаимодействие с бутилбромидом
Журнал органической химии (RUSS J ORG CHEM+). 2003. Т.39. №6. С.725-731. РИНЦ

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