Abstract
Using pyridine, quinoline, and related compounds as examples, it has been shown that their interaction with triphenylphosphine occurs via different pathways. Reaction of triphenylphosphine with N-vinylisonicotinic acid chloride leads to the mixture of 1,2-bis(triphenylphosphoniumchlorido)ethane and 4-carboxy-2-(triphenylphosphoniumchloridoethyl)pyridine. In the case of α-(N-2-carboxyquinolinylbromido)-β-bromopropionic acid, the reaction with triphenylphosphine proceeds via phosphine attack on the oxygen atom with elimination of quinaldinic acid, and subsequent nucleophilic substitution with the formation of 3-(triphenylphosphoniumbromido) propionic acid bromide.
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Original Russian Text © R.D. Khachikyan, A.G. Simonyan, R.S. Manukyan, M.G. Indzhikyan, 2013, published in Zhurnal Obshchei Khimii, 2013, Vol. 83, No. 7, pp. 1107–1112.
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Khachikyan, R.D., Simonyan, A.G., Manukyan, R.S. et al. Special features of the interaction of pyridine and quinoline derivatives, and related compounds with triphenylphosphine. Russ J Gen Chem 83, 1359–1364 (2013). https://doi.org/10.1134/S1070363213070104
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DOI: https://doi.org/10.1134/S1070363213070104