Steric effects of ortho substituents in reactions of phenols and phenolates with polyfluoroketones

  • V. I. Dyachenko
  • M. V. Galakhov
  • A. F. Kolomiets
  • A. V. Fokin
Organic Chemistry

Conclusions

  1. 1.

    In the reactions of phenols with polyfluorocarbonyl compounds, as the bulk of theo-substituent increases O-alkylation is hindered, so that C-alkylation is facilitated.

     
  2. 2.

    C-alkylation ofo-substituted phenols and sodium phenolates by polyfluoroketones in nonpolar medium, regardless of substituent bulk, is regiospecifico-substitution; in the case of phenolates the subsequentp-alkylation also goes easily.

     

Keywords

Sodium Phenol Steric Effect Nonpolar Medium Ortho Substituent 

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Literature cited

  1. 1.
    V. I. Dyachenko, A. F. Kolomiets, and A. V. Fokin, Izv. Akad. Nauk SSSR, Ser. Khim., No. 5, 1080 (1987).Google Scholar
  2. 2.
    V. I. Dyachenko, A. F. Kolomiets, and A. V. Fokin, Izv. Akad. Nauk SSSR, Ser. Khim., No. 11, 2511 (1987).Google Scholar
  3. 3.
    V. I. Dyachenko, A. F. Kolomiets, and A. V. Fokin, Zh. Org. Khim.,23, No. 4, 893 (1987).Google Scholar
  4. 4.
    V. I. Dyachenko, A. F. Kolomiets, and A. V. Fokin, Izv. Akad. Nauk SSSR, Ser. Khim., No. 12, 2849 (1987).Google Scholar
  5. 5.
    V. I. Dyachenko, A. F. Kolomiets, and A. V. Kokin, Izv. Akad. Nauk SSSR, Ser. Khim., No. 11, 2557 (1988).Google Scholar
  6. 6.
    C. A. Krespan, and W. J. Middleton, Fluor. Chem. Rev.,1, No. 1, 145 (1967).Google Scholar
  7. 7.
    B. F. Farah, E. E. Gilbert, Litt Morton, et al., J. Org. Chem.,30, No. 4, 1003 (1965).Google Scholar

Copyright information

© Plenum Publishing Corporation 1989

Authors and Affiliations

  • V. I. Dyachenko
    • 1
  • M. V. Galakhov
    • 1
  • A. F. Kolomiets
    • 1
  • A. V. Fokin
    • 1
  1. 1.A. N. Nesmeyanov Institute of Heteroorganic CompoundsAcademy of Sciences of the USSRMoscow

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