Defluorination And Other Transformations of Perfluorinated Tetralin, Alkyltetralins and 4-Methyl-1,2-Dihydronaphthalene with Zinc in DMF. Synthesis of Perfluorinated 1-Ethyl- and 1-Methylnaphthalenes

V. R. Sinyakov; Синяков Владимир Рейнович; T. V. Mezhenkova; Меженкова Татьяна Владимировна; V. M. Karpov; Карпов Виктор Михайлович; Ya. V. Zonov; Зонов Ярослав Викторович

doi:10.31857/S0514749224080017

Defluorination And Other Transformations of Perfluorinated Tetralin, Alkyltetralins and 4-Methyl-1,2-Dihydronaphthalene with Zinc in DMF. Synthesis of Perfluorinated 1-Ethyl- and 1-Methylnaphthalenes

Authors: Sinyakov V.R.¹, Mezhenkova T.V.¹, Karpov V.M.¹, Zonov Y.V.¹
Affiliations:
1. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences
Issue: Vol 60, No 8 (2024)
Pages: 5-14
Section: Articles
URL: https://journal-vniispk.ru/0514-7492/article/view/279402
DOI: https://doi.org/10.31857/S0514749224080017
EDN: https://elibrary.ru/RBGJLW
ID: 279402

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Abstract

The interaction of perfluorotetralin with zinc in DMF followed by the treatment with water gave 1,1,2,2,3,3,4,4,5,6,8-undecafluorotetralin, perfluoro-2,2'-binaphthyl and octafluoronaphthalene. 1,2,3,4,6,7-Hexafluoro-5-(perfluoroethyl)naphthalene and perfluorinated 1-ethyl- and 1-vinylnaphthalenes were obtained from perfluoro-1-ethyltetralin by a similar reaction. Perfluoro-6-methyltetralin under similar conditions formed 1,2,4,5,6,8-hexafluoro-3-(trifluoromethyl)naphthalene and perfluoro-2-methylnaphthalene. The reaction of perfluoro-4-methyl-1,2-dihydronaphthalene with zinc in DMF resulted in the formation of perfluoro-1-methylnaphthalene. When perfluoro-1-ethyltetraline reacted with bromine-activated zinc in DMF, a mixture containing (perfluoro-4-ethylnaphthalene-1-yl)zinc bromide was formed, which was converted into 1,2,3,4,6,7-hexafluoro-5-(perfluoroethyl)naphthalene and perfluoro-4,4'-diethyl-1,1'-binaphthyl under the action of water and CuCl₂, respectively.

Keywords

perfluorinated methyltetralin, ethyltetralin, naphthalene, methylnaphthalene, ethylnaphthalene, zinc, dimethylformamide

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