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Reaction of 2,3-Dihalopropionic Acids and Their Derivatives with P- and N-Nucleophiles

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Abstract

3-(Triphenylphosphoniochlorido)acrylic and 2,3-dichloropropionic acids react with triphenylphosphine to form 1,2-bis(triphenylphosphoniochlorido)ethane. Under analogous conditions, 2,3-dibromopropionic acid undergoes debromination followed by triphenylphosphine addition to give, after water treatment, 3-(triphenylphosphoniobromido)propionic acid. 2,3-Dihalopropionitriles react similarly, providing 3-(triphenylphosphoniohalido) propionitriles. The reaction of 2,3-dibromopropionamide with triphenylphosphine was performed to show that E-(triphenylphosphoniobromido)acrylic acid is capable, by contrast to what was reported previously, of reacting with triphenylphosphine. Pyridine forms with 2,3-dihalopropionic acids vinylpyridinium halides, while the reactions with aliphatic amines gives rise to dehydrohalogenation products.

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Authors and Affiliations

  1. Institute of Organic Chemistry, National Academy of Sciences of Armenia, Erevan, Armenia

    R. Dzh. Khachikyan, N. V. Tovmasyan & M. G. Indzhikyan

Authors
  1. R. Dzh. Khachikyan
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  2. N. V. Tovmasyan
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  3. M. G. Indzhikyan
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Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 12, 2005, pp. 1978–1983.

Original Russian Text Copyright © 2005 by Khachikyan, Tovmasyan, Indzhikyan.

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Khachikyan, R.D., Tovmasyan, N.V. & Indzhikyan, M.G. Reaction of 2,3-Dihalopropionic Acids and Their Derivatives with P- and N-Nucleophiles. Russ J Gen Chem 75, 1889–1894 (2005). https://doi.org/10.1007/s11176-006-0009-z

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  • DOI: https://doi.org/10.1007/s11176-006-0009-z

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