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
- Autores: Peshkov R.1,2, Wang C.2,3, Panteleeva E.1,2, Tretyakov E.1,2, Shteingarts V.1
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Afiliações:
- 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
- Edição: Volume 65, Nº 10 (2016)
- Páginas: 2430-2436
- Seção: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/239129
- DOI: https://doi.org/10.1007/s11172-016-1602-x
- ID: 239129
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Resumo
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.
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Sobre autores
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
Rússia, 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
Rússia, 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
Autor responsável pela correspondência
Email: pantel@nioch.nsc.ru
Rússia, 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
Rússia, 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
Rússia, 9 prosp. Acad. Lavrentiev, Novosibirsk, 630090