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Alkylating properties of alkyl fluoroalkenyl ethers

Communication 4.19F NMR spectra of adducts of triethylamine with the acid fluoride of α-hydrohexafluoroisobutyric acid and with ethyl perfluoroisobutenyl ether

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    The acid fluoride ofα-hydrohexafluoroisobutyric acid is capable of exchanging a proton with the mesomeric perfluoroisobutenolate anion.

  2. 2.

    The peculiarities of the19F NMR spectra of triethylammonium perfluoroisobutenolate, obtained from the acid fluoride ofα-hydrohexafluoroisobutyric acid and triethylamine, are explained by exchange processes, which lower the energy barrier that prevents rotation around the C-C bond in the mesomeric carbanion.

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Literature cited

  1. I. L. Knunyants, M. V. Urushadze, V. A. Livshits, E. G. Abduganiev, E. M. Rokhlin, and Yu. A, Cheburkov, Izv. Akad. Nauk SSSR, Ser. Khim., 54 (1972).

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  4. Yu. A. Cheburkov, Dissertation [in Russian], Moscow (1967).

  5. M. V. Urushadze, E. G. Abduganiev, E. M. Rokhlin, and I. L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim., No. 6 (1972).

  6. J. W. Emsley, J. Feeney, and L. H. Sutcliffe, High Resolution Nuclear Magnetic Resonance Spectroscopy [Russian translation], Mir (1968), Vol. 1, p. 456; J. H. Pople, W. G. Schneider, and H. J. Bernstein, High-Resolution Nuclear Magnetic Resonance [Russian translation], IL (1962), pp. 267, 438.

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Authors and Affiliations

  1. Institute of Heteroorganic Compounds, Academy of Sciences of the USSR, USSR

    M. V. Urushadze, P. O. Okulevich, I. D. Rubin, P. V. Petrovskii, É. I. Fedin, E. M. Rokhlin, Yu. A. Cheburkov & I. L. Knunyants

Authors
  1. M. V. Urushadze
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  2. P. O. Okulevich
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  3. I. D. Rubin
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  4. P. V. Petrovskii
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  5. É. I. Fedin
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  6. E. M. Rokhlin
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  7. Yu. A. Cheburkov
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  8. I. L. Knunyants
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Additional information

See [1] for preceding communication.

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1137–1145, May, 1972.

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Urushadze, M.V., Okulevich, P.O., Rubin, I.D. et al. Alkylating properties of alkyl fluoroalkenyl ethers. Russ Chem Bull 21, 1089–1095 (1972). https://doi.org/10.1007/BF00853775

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  • DOI: https://doi.org/10.1007/BF00853775

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