Skip to main content
SpringerLink
Log in

Characteristic features of reactions of phenolate ions with polyfluorocarbonyl compounds

  • Organic Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    Phenolates containing electron-acceptor substituents in the aromatic ring are regiospecifically C-alkylated by hexafluoroacetone and methyl trifluoropyruvate to form monoalkylation products, and in the presence of an excess of hexafluoroacetone form dialkylation products.

  2. 2.

    In Freon-113, Li and Na phenolates are alkylated by hexafluoroacetone in the o-position, and K phenolates in the p-position; in DMF, irrespective of the counterion, the phenolates form p-alkylation products with hexafluoroacetone. The regiospecific o-alkylation of Li and Na phenolates in nonpolar media, is possibly explained by chelate formation.

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

Literature cited

  1. V. I. Dyachenko, A. F. Kolomiets, and A. V. Fokin, Zh. Org. Khim.,23, 893 (1987).

    Google Scholar 

  2. V. I. Dyachenko, A. F. Kolomiets, and A. V. Fokin, Izv. Akad. Nauk SSSR, Ser. Khim., 2849 (1987).

  3. H. Becker, Einfuehrung in die Elektronentheorie Organisch-Chemischer Reaktionen, VEB Deutscher Verlag der Wissenschaften, Berlin (1961).

    Google Scholar 

  4. B. S. Farah, E. E. Gilbert, Morton Litt, et al., J. Org. Chem.,30, 1003 (1965).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Heteroorganic Compounds, Academy of Sciences of the USSR, Moscow

    V. I. Dyachenko, A. F. Kolomiets & A. V. Fokin

Authors
  1. V. I. Dyachenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. F. Kolomiets
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. V. Fokin
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2557–2561, November, 1988.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dyachenko, V.I., Kolomiets, A.F. & Fokin, A.V. Characteristic features of reactions of phenolate ions with polyfluorocarbonyl compounds. Russ Chem Bull 37, 2306–2310 (1988). https://doi.org/10.1007/BF00959884

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00959884

Keywords

Search

Navigation