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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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. / Sinyakov, V. R.; Mezhenkova, T. V.; Karpov, V. M. et al.

In: Russian Journal of Organic Chemistry, Vol. 53, No. 12, 01.12.2017, p. 1822-1827.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{7410deed61d8440bb5712230c9915056,

title = "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",

abstract = "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.",

author = "Sinyakov, {V. R.} and Mezhenkova, {T. V.} and Karpov, {V. M.} and Zonov, {Ya V.}",

year = "2017",

month = dec,

day = "1",

doi = "10.1134/S1070428017120065",

language = "English",

volume = "53",

pages = "1822--1827",

journal = "Russian Journal of Organic Chemistry",

issn = "1070-4280",

publisher = "Maik Nauka-Interperiodica Publishing",

number = "12",

}

RIS

TY - JOUR

T1 - 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

AU - Sinyakov, V. R.

AU - Mezhenkova, T. V.

AU - Karpov, V. M.

AU - Zonov, Ya V.

PY - 2017/12/1

Y1 - 2017/12/1

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85040996527&partnerID=8YFLogxK

U2 - 10.1134/S1070428017120065

DO - 10.1134/S1070428017120065

M3 - Article

AN - SCOPUS:85040996527

VL - 53

SP - 1822

EP - 1827

JO - Russian Journal of Organic Chemistry

JF - Russian Journal of Organic Chemistry

SN - 1070-4280

IS - 12

ER -

ID: 9490243