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 |
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| Output data | Year: 2002, Volume: 38, Number: 6, Pages: 823-829 Pages count : 7 DOI: 10.1023/A:1020387003972 | ||
| Tags | Oxidation; Sodium; Ammonia; Organic Chemistry; Alkylation | ||
| Authors |
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| Affiliations |
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Funding (2)
| 1 | Russian Foundation for Basic Research | 99-03-33111 |
| 2 | The Ministry of Education and Science of the Russian Federation | 2000.5.90 |
Abstract:
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.
Cite:
Vaganova T.A.
, Starokonʹ E.V.
, Shteingarts V.D.
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
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
ArticleLinkType.TRANSLATED_TO_ORIGINAL:
Ваганова Т.А.
, Староконь Е.В.
, Штейнгарц В.Д.
Восстановительная активация аренов. XV. Анионные продукты восстановления м-толунитрила натрием в жидком аммиаке и их алкилирование
Журнал органической химии. 2002. Т.38. №6. С.865-871. РИНЦ
Восстановительная активация аренов. XV. Анионные продукты восстановления м-толунитрила натрием в жидком аммиаке и их алкилирование
Журнал органической химии. 2002. Т.38. №6. С.865-871. РИНЦ
Dates:
| Submitted: | Nov 21, 2001 |
| Published print: | Jun 1, 2002 |
Identifiers:
| Web of science | WOS:000177926900008 |
| Scopus | 2-s2.0-0036389215 |
| Elibrary | 13405022 |
| AN | 2002:727018 |
| CAN | 138:187486 |