Abstract
By refluxing pyridine with 2,3-dibromopropionic acid amide in acetonitrile, amide of 3-bromo-2-pyridiniumbromidopropionic acid I was synthesized. The latter is inert toward the second molecule of pyridine under the used conditions. Compound I was found to react with triphenylphosphine to form a mixture of 3-triphenylphosphoniumbromidopropionitrile II and 1-triphenylphosphoniumbromido-2-pyridiniumbromidoethane III. Schemes of reactions were suggested involving attack of phosphine on the carbonyl group as the first stage. The reaction of α-bromoacrylic acid amide with triphenylphosphine was shown to yield also compound II. Evidently, this reaction proceeds through intermediate formation of enolphosphonium salt.
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Khachikyan, R.Dzh., Tovmasyan, N.V., and Indzhikyan, M.G., Zh. Obshch. Khim., 2005, vol. 75, no. 12, p. 1978.
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Original Russian Text © R.Dzh. Khachikyan, N.V. Tovmasyan, M.G. Indzhikyan, 2009, published in Zhurnal Obshchei Khimii, 2009, Vol. 79, No. 4, pp. 595–597.
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Khachikyan, R.D., Tovmasyan, N.V. & Indzhikyan, M.G. Reaction of amides of 2,3-dibromopropionic and 2-bromoacrylic acids with pyridine and triphenylphosphine. Russ J Gen Chem 79, 759–761 (2009). https://doi.org/10.1134/S1070363209040148
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DOI: https://doi.org/10.1134/S1070363209040148