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
- Авторлар: Peshkov R.1,2, Wang C.2,3, Panteleeva E.1,2, Tretyakov E.1,2, Shteingarts V.1
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Мекемелер:
- 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
- Шығарылым: Том 65, № 10 (2016)
- Беттер: 2430-2436
- Бөлім: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/239129
- DOI: https://doi.org/10.1007/s11172-016-1602-x
- ID: 239129
Дәйексөз келтіру
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.
Негізгі сөздер
Авторлар туралы
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
Ресей, 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
Ресей, 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
Хат алмасуға жауапты Автор.
Email: pantel@nioch.nsc.ru
Ресей, 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
Ресей, 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
Ресей, 9 prosp. Acad. Lavrentiev, Novosibirsk, 630090