Defluorination and Other Transformations of Perfluorinated Tetralin, Alkyltetralins and 4-Methyl-1,2-dihydronaphthalene in the System Zn–DMF. Synthesis of Perfluoro-1-ethyl- and -1-methylnaphthalenes

IF 0.8 4区化学 Q4 CHEMISTRY, ORGANIC Russian Journal of Organic Chemistry Pub Date : 2024-08-30 DOI:10.1134/s1070428024060058

V. R. Sinyakov, T. V. Mezhenkova, V. M. Karpov, Ya. V. Zonov

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Abstract

The reaction of perfluorotetralin with zinc in DMF, followed by treatment with water, gave 1,1,2,2,3,3,4,4,5,6,8-undecafluorotetralin, perfluoro-2,2′-binaphthalene, and octafluoronaphthalene. Under similar conditions, perfluoro-1-ethyltetralin was converted into a mixture of 1,2,3,4,6,7-hexafluoro-5-(perfluoroethyl)naphthalene and perfluorinated 1-ethyl- and 1-vinylnaphthalenes, perfluoro-6-methyltetralin gave rise to 1,2,4,5,6,8-hexafluoro-3-(trifluoromethyl)naphthalene and perfluoro-2-methylnaphthalene, and perfluoro-1-methylnaphthalene was obtained from perfluoro-4-methyl-1,2-dihydronaphthalene. Perfluoro-1-ethyltetralin reacted with bromine-activated zinc in DMF to produce a mixture containing (perfluoro-4-ethylnaphthalen-1-yl)zinc bromide which was converted to 1,2,3,4,6,7-hexafluoro-5-(perfluoroethyl)naphthalene by the action of water, while its reaction with CuCl₂ afforded perfluoro-4,4′-diethyl-1,1′-binaphthalene.

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全氟四氢萘、烷基四氢萘和 4-甲基-1,2-二氢萘在 Zn-DMF 体系中的脱氟及其他转化。全氟-1-乙基萘和-1-甲基萘的合成

摘要全氟四氢萘与锌在DMF中反应，然后用水处理，得到1,1,2,2,3,3,4,4,5,6,8-十一氟四氢萘，全氟-2,2′-联萘和八氟萘。在类似条件下，全氟-1-乙基四氢萘被转化为 1,2,3,4,6,7-六氟-5-（全氟乙基）萘和全氟 1-乙基萘和 1-乙烯基萘的混合物、全氟-6-甲基四氢萘可生成 1,2,4,5,6,8-六氟-3-三氟甲基萘和全氟-2-甲基萘，全氟-4-甲基-1,2-二氢萘可生成全氟-1-甲基萘。全氟-1-乙基四氢萘在 DMF 中与溴活化锌反应，生成含有（全氟-4-乙基萘-1-基）溴化锌的混合物，在水的作用下转化为 1,2,3,4,6,7-六氟-5-（全氟乙基）萘，而与 CuCl2 反应则生成全氟-4,4′-二乙基-1,1′-萘。

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来源期刊

Russian Journal of Organic Chemistry 化学-有机化学

CiteScore

1.40

自引率

25.00%

发文量

139

审稿时长

3-6 weeks

期刊介绍： Russian Journal of Organic Chemistry is an international peer reviewed journal that covers all aspects of modern organic chemistry including organic synthesis, theoretical organic chemistry, structure and mechanism, and the application of organometallic compounds in organic synthesis.