Reductive activation of arenes: XV. Anionic products of m-tolynitrile reduction with sodium in liquid ammonia, and their alkylation

Reductive activation of arenes: XV. Anionic products of m-tolynitrile reduction with sodium in liquid ammonia, and their alkylation Full article

Journal

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

Output data

Year: 2002, Volume: 38, Number: 6, Pages: 823-829 Pages count : 7 DOI: 10.1023/A:1020387003972

Authors

Vaganova TA ¹ , Starokon' EV ¹ , Shteingarts VD ¹

Affiliations

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

From results of oxidation, protonation, and alkylation of the products arising in one- or two-electron reduction of m-tolunitrile with sodium in liquid ammonia followed a conclusion that these products are respectively anion-radical of the compound and 3-methyl-1-cyano-2,5-cyclohexadienyl anion. The reaction of both reduction products with alkyl halides gives rise to compounds of ipso-alkylation with respect to cyano group: the corresponding alkyltoluenes and 1-alkyl-3-methyl-1-cyclohexadienes. The ratio of these products depends on the structure of alkyl halide. The possibility to prepare selectively m-alkyltoluenes by reaction of the product of two-electron reduction of m-tolunitrile with alkyl halides was demonstrated.

Vaganova T. , Starokon' E. , Shteingarts V.
Reductive activation of arenes: XV. Anionic products of m-tolynitrile reduction with sodium in liquid ammonia, and their alkylation
Russian Journal of Organic Chemistry. 2002. V.38. N6. P.823-829. DOI: 10.1023/A:1020387003972 WOS Scopus РИНЦ

Web of science	WOS:000177926900008
Scopus	2-s2.0-0036389215
Elibrary	13405022
OpenAlex	W2950027433