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
- 作者: Peshkov R.1,2, Wang C.2,3, Panteleeva E.1,2, Tretyakov E.1,2, Shteingarts V.1
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隶属关系:
- 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
- 期: 卷 65, 编号 10 (2016)
- 页面: 2430-2436
- 栏目: 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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详细
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.
作者简介
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
俄罗斯联邦, 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
俄罗斯联邦, 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
编辑信件的主要联系方式.
Email: pantel@nioch.nsc.ru
俄罗斯联邦, 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
俄罗斯联邦, 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
俄罗斯联邦, 9 prosp. Acad. Lavrentiev, Novosibirsk, 630090