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α-Fluoroalkylamines, a new source of nonhydrated fluoride ions. Communication 5. N,N-dimethylmethylenimmonium perfluoroalcoholates and their reactions with perfluoroolefins

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

Conclusions

  1. 1.

    The reaction of fluoromethyldimethylamine with polyfluoroketones leads to N,N-dimethylmethylenimmonium polyfluoroalcoholates which are capable of adding to perfluoroolefins to form polyfluoro-substituted alkoxyalkyldimethylamines.

  2. 2.

    Alkali metal perfluoroalcoholates add reversibly to perfluoroolefins to give β-perfluoroalkoxy carbanions which may be trapped by reaction with electrophilic reagents.

  3. 3.

    These results indicate that the perfluoroalkoxyhalogenation of higher perfluoroolefins proceeds by a nucleophilic mechanism.

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Authors and Affiliations

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

    S. M. Igumnov, N. I. Delyagina, Yu. V. Zeifman & I. L. Knunyants

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  1. S. M. Igumnov
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  2. N. I. Delyagina
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  3. Yu. V. Zeifman
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  4. I. L. Knunyants
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Additional information

For communication 4, see [1].

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 827–832, April, 1984.

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Igumnov, S.M., Delyagina, N.I., Zeifman, Y.V. et al. α-Fluoroalkylamines, a new source of nonhydrated fluoride ions. Communication 5. N,N-dimethylmethylenimmonium perfluoroalcoholates and their reactions with perfluoroolefins. Russ Chem Bull 33, 762–766 (1984). https://doi.org/10.1007/BF00947829

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  • DOI: https://doi.org/10.1007/BF00947829

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