Synthesis of (6,7-dichlorononafluoro-5,6,7,8-tetrahydronaphthalen-2-yl)acetic acid and its transformation into perfluorinated 2-methylnaphthalene and 6-methyl-1,4-dihydronaphthalene
- Autores: Sinyakov V.R.1, Mezhenkova T.V.1, Karpov V.M.1, Zonov Y.V.1,2
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Afiliações:
- Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch
- Novosibirsk State University
- Edição: Volume 53, Nº 12 (2017)
- Páginas: 1822-1827
- Seção: Article
- URL: https://bakhtiniada.ru/1070-4280/article/view/217020
- DOI: https://doi.org/10.1134/S1070428017120065
- ID: 217020
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Resumo
2,3-Dichlorodecafluorotetralin reacted with ethyl cyanoacetate to give ethyl 2-cyano-2-(6,7-dichlorononafluoro-5,6,7,8-tetrahydronaphthalen-2-yl)acetate which was hydrolyzed to (6,7-dichlorononafluoro-5,6,7,8-tetrahydronaphthalen-2-yl)acetic acid. The latter was treated with PCl5 on heating to obtain 2,2-dichloro-(6,7-dichlorononafluoro-5,6,7,8-tetrahydronaphthalen-2-yl)acetyl chloride which was converted to 2,3-dichlorononafluoro-6-trifluoromethyl-1,2,3,4-tetrahydronaphthalene by the action of SbF5. The reduction of 2,3-dichlorononafluoro-6-trifluoromethyl-1,2,3,4-tetrahydronaphthalene with zinc in 1,4-dioxane gave perfluoro-6-methyl-1,4-dihydronaphthalene, and in DMF, perfluoro-2-methylnaphthalene.
Sobre autores
V. Sinyakov
Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch
Email: karpov@nioch.nsc.ru
Rússia, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090
T. Mezhenkova
Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch
Email: karpov@nioch.nsc.ru
Rússia, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090
V. Karpov
Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch
Autor responsável pela correspondência
Email: karpov@nioch.nsc.ru
Rússia, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090
Ya. Zonov
Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch; Novosibirsk State University
Email: karpov@nioch.nsc.ru
Rússia, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090; ul. Pirogova 2, Novosibirsk, 630090
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