Skip to main content
SpringerLink
Log in

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

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Pozdnyakovich, Yu.V. and Shteingarts, V.D., J. Fluorine Chem., 1974, vol. 4, p. 283; ibid., p. 297.

    Article  CAS  Google Scholar 

  2. Fadeev, D.S., Chuikov, I.P., and Mamatyuk, V.I., J. Fluorine Chem., 2016, vol. 182, p. 53.

    Article  CAS  Google Scholar 

  3. Gething, B., Patrick, C.R., Smith, B.J.K., and Tatlow, J.C., J. Chem. Soc., 1962, p. 190.

    Google Scholar 

  4. Malysheva, V.V., Platonov, V.E., and Yakobson, G.G., Bull. Acad. Sci. USSR, Div. Chem. Sci., 1974, vol. 23, p. 1598.

    Article  Google Scholar 

  5. Platonov, V.E., Malysheva, V.V., and Yakobson, G.G., Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, 1977, no. 2, p. 133; Chem. Abstr., 1977, vol. 87, no. 134 761 d.

    Google Scholar 

  6. Weigert, F.J., J. Fluorine Chem., 1993, vol. 61, p. 1.

    Article  CAS  Google Scholar 

  7. Sinyakov, V.R., Mezhenkova, T.V., Karpov, V.M., and Zonov, Ya.V., Russ. J. Org. Chem., 2016, vol. 52, p. 1427.

    Article  CAS  Google Scholar 

  8. Klimenko, L.S., Karpov, V.M., Platonov, V.E., and Yakobson, G.G., Zh. Org. Khim., 1979, vol. 15, p. 146.

    CAS  Google Scholar 

  9. Shteingarts, V.D. and Oksenenko, B.G., Zh. Org. Khim., 1970, vol. 6, p. 1611.

    CAS  Google Scholar 

  10. Osina, O.I., Chuikova, T.V., and Shteingarts, V.D., Zh. Org. Khim., 1980, vol. 16, p. 805.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090, Russia

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

  2. Novosibirsk State University, ul. Pirogova 2, Novosibirsk, 630090, Russia

    Ya. V. Zonov

Authors
  1. V. R. Sinyakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. T. V. Mezhenkova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. M. Karpov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Ya. V. Zonov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. M. Karpov.

Additional information

Original Russian Text © V.R. Sinyakov, T.V. Mezhenkova, V.M. Karpov, Ya.V. Zonov, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 12, pp. 1786–1791.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sinyakov, V.R., Mezhenkova, T.V., Karpov, V.M. et al. 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. Russ J Org Chem 53, 1822–1827 (2017). https://doi.org/10.1134/S1070428017120065

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428017120065

Search

Navigation