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


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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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