Abstract
The rate of hydrogenolysis of 3,5-dioxopyrazolidines at the N-N bond is determined by the number, position, and nature of the substituents in the heteroring. The introduction of a phenyl group into the 1 and 2 positions increases the rate of hydrogenation, while a phenyl group in the 4 position lowers it. On the other hand, an alkyl substituent in the 1 and 2 positions lowers the rate of hydrogenation, while an alkyl substituent in the 4 position increases it. It is assumed that the effect of substituents is a consequence of an increase or decrease in the adsorption of a molecule by the β-dicarbonyl or hydrazine fragments; this is in agreement with the results of calculation of the charges on the heteroring atoms. The hydrogenation of 4alkyl-1, 2-diphenyl-3,5-dioxopyrazolidines is limited by their activation, while the hydrogenation of the 4-phenyl derivative is limited by the activation of hydrogen.
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See [1] for communication XIX.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 781–787, June, 1973.
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Moldaver, B.L., Papirnik, M.P., Zverev, V.V. et al. Research in the chemistry of pyrazolidine. Chem Heterocycl Compd 9, 717–722 (1973). https://doi.org/10.1007/BF00472315
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DOI: https://doi.org/10.1007/BF00472315