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

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 Full article

Journal

Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393

Output data

Year: 2024, Volume: 60, Number: 6, Pages: 1013-1021 Pages count : 9 DOI: 10.1134/s1070428024060058

Tags

perfluorinated methyltetralin ethyltetralin naphthalene methylnaphthalene ethylnaphthalene zinc dimethylformamide

Authors

Sinyakov V.R. ¹ , Mezhenkova T.V. ¹ , Karpov V.M. ¹ , Zonov Ya.V. ¹

Affiliations

1	Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences

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.

Sinyakov V.R. , Mezhenkova T.V. , Karpov V.M. , Zonov Y.V.
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
Russian Journal of Organic Chemistry. 2024. V.60. N6. P.1013-1021. DOI: 10.1134/s1070428024060058 WOS OpenAlex

Submitted:	Oct 25, 2023
Accepted:	Nov 13, 2023
Published print:	Aug 30, 2024

Web of science:	WOS:001303584000004
OpenAlex:	W4402051598

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