Synthesis of 4-(ω-X-alkyl)benzonitriles (X = 1,3-dioxan-2-yl, CN, CO2Et) by the reaction of terephthalonitrile dianion with ω-X-alkyl bromides in liquid ammonia
- Авторы: Peshkov R.1,2, Wang C.2,3, Panteleeva E.1,2, Tretyakov E.1,2, Shteingarts V.1
-
Учреждения:
- N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences
- Novosibirsk State University
- Russian-China Institute of Heilongjiang University
- Выпуск: Том 65, № 10 (2016)
- Страницы: 2430-2436
- Раздел: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/239129
- DOI: https://doi.org/10.1007/s11172-016-1602-x
- ID: 239129
Цитировать
Аннотация
The main products of the reaction of terephthalonitrile dianion disodium salt with ω-X-alkyl bromides (2-(2-bromoethyl)-1,3-dioxane, 5-bromovaleronitrile, ethyl 6-bromohexanoate) in liquid ammonia are the corresponding 4-(ω-X-alkyl)benzonitriles. Similar reactions of benzonitrile radical anion sodium salt lead to ω-X-alkylbenzenes. In both cases the formation of products is due to selective ipso-alkylation of anionic forms that indicates the nucleophilic activity of terephthalonitrile dianion and benzonitrile radical anion in these reactions and the realization of alkylation via SN2 mechanism.
Ключевые слова
Об авторах
R. Peshkov
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences; Novosibirsk State University
Email: pantel@nioch.nsc.ru
Россия, 9 prosp. Acad. Lavrentiev, Novosibirsk, 630090; 2 ul. Pirogova, Novosibirsk, 630090
Chynyan Wang
Novosibirsk State University; Russian-China Institute of Heilongjiang University
Email: pantel@nioch.nsc.ru
Россия, 2 ul. Pirogova, Novosibirsk, 630090; 74 Xuefu Road, Harbin, 150080
E. Panteleeva
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences; Novosibirsk State University
Автор, ответственный за переписку.
Email: pantel@nioch.nsc.ru
Россия, 9 prosp. Acad. Lavrentiev, Novosibirsk, 630090; 2 ul. Pirogova, Novosibirsk, 630090
E. Tretyakov
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences; Novosibirsk State University
Email: pantel@nioch.nsc.ru
Россия, 9 prosp. Acad. Lavrentiev, Novosibirsk, 630090; 2 ul. Pirogova, Novosibirsk, 630090
V. Shteingarts
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences
Email: pantel@nioch.nsc.ru
Россия, 9 prosp. Acad. Lavrentiev, Novosibirsk, 630090