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

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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.

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About the authors

V. R. Sinyakov

Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences

Email: karpov@nioch.nsc.ru
Russian Federation, Novosibirsk

T. V. Mezhenkova

Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences

Email: karpov@nioch.nsc.ru
ORCID iD: 0000-0001-9936-0900
Russian Federation, Novosibirsk

V. M. Karpov

Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences

Author for correspondence.
Email: karpov@nioch.nsc.ru
Russian Federation, Novosibirsk

Ya. V. Zonov

Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences

Email: karpov@nioch.nsc.ru
ORCID iD: 0000-0003-0267-4976
Russian Federation, Novosibirsk

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