Abstract
Triphenyl(2-p-toluoylethyl)- and triphenyl(2-p-bromobenzoylethyl)phosphonium bromide 2,4-dinitrophenylhydrazones were established to form a bipolar compounds with a negatively charged nitrogen atom and a positively charged phosphonium atom, under the action of aqueous alkali at 0°C. When refluxed in acetonitrile, the product formed from triphenyl(2-p-toluoylethyl)phosphonium bromide undergoes cleavage by a five-membered ring mechanism to give triphenylphosphine and tolyl vinyl ketone 2,4-dinitrophenylhydrazone. The reactions of the above betains with methyl iodide give rise to N-alkylation and cleavage products, but, in addition, iodide analogs of the starting phosphonium salt 2,4-dinitrophenylhydrazones which are probably formed via N→C negative charge transfer, C-methylation, and reaction of the resulting products with N-betaines.
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Original Russian Text © R.Dzh. Khachikyan, 2009, published in Zhurnal Obshchei Khimii, 2009, Vol. 79, No. 1, pp. 90–93.
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Khachikyan, R.D. Reaction of 2,4-dinitrophenylhydrazones of triphenyl(2-aroylethyl)phosphonium bromides with aqueous alkali and some transformations of the betaines formed. Russ J Gen Chem 79, 88–91 (2009). https://doi.org/10.1134/S1070363209010137
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DOI: https://doi.org/10.1134/S1070363209010137