Reductive Activation of Arenes: XV. Anionic Products of m-Tolynitrile Reduction with Sodium in Liquid Ammonia,
and Their Alkylation
Научная публикация
| Общая информация |
Язык:
Английский,
Жанр:
Статья (Full article),
Статус опубликования:
Опубликована,
Оригинальность:
Переводная
|
| Журнал |
Russian Journal of Organic Chemistry
ISSN: 1070-4280
, E-ISSN: 1608-3393
|
| Вых. Данные |
Год: 2002,
Том: 38,
Номер: 6,
Страницы: 823-829
Страниц
: 7
DOI:
10.1023/A:1020387003972
|
| Ключевые слова |
Oxidation; Sodium; Ammonia; Organic Chemistry; Alkylation |
| Авторы |
Vaganova T.A.
1
,
Starokonʹ E.V.
1
,
Shteingarts V.D.
1
|
| Организации |
| 1 |
Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, Novosibirsk, 630090 Russia
|
|
Информация о финансировании (2)
|
1
|
Российский фонд фундаментальных исследований
|
99-03-33111
|
|
2
|
Министерство образования и науки Российской Федерации
|
2000.5.90
|
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.