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Mechanism of tropylation

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

Summary

  1. 1.

    A study was made of the kinetics of the reactions of tropylium bromide with malonic acid, acetoacetic ester, and isobutyraldehyde in water at 20° in the pH region from 1 to 3.

  2. 2.

    The stage determining the rate of tropylation of malonic acid and acetoacetic ester is the formation of the enolate anion. The tropylation of isobutyraldehyde proceeds via its preliminary protonization.

  3. 3.

    Tropylation may be used to measure the rate of ionization of the C-H bond of pseudoacids.

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Literature cited

  1. M. E. Vol'pin, I. S. Akhrem, and D. N. Kursanov, Izv. AN SSSR, Otd. khim. n. 1501 (1957).

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Authors and Affiliations

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

    M. E. Vol'pin, I. S. Akhrem, E. A. Terent'eva & D. N. Kursanov

Authors
  1. M. E. Vol'pin
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  2. I. S. Akhrem
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  3. E. A. Terent'eva
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  4. D. N. Kursanov
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Vol'pin, M.E., Akhrem, I.S., Terent'eva, E.A. et al. Mechanism of tropylation. Russ Chem Bull 12, 726–731 (1963). https://doi.org/10.1007/BF01134714

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  • DOI: https://doi.org/10.1007/BF01134714

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