Abstract
It was found by means of a spectrophotometric method that esters of substituted 4-hydroxypiperidines are hydrolyzed four times faster in water and in 50% aqueous methanol in the presence of alkali than in isosteric carbocyclic ester; this is due to the presence of the inductive effect of the nitrogen atom and the additional polar effect of an as yet unknown nature. Esters with an axial acyloxy group are hydrolyzed more slowly by a factor of two to three than their epimers with an equatorial acyloxy group owing to the steric effect, but this difference vanishes when a charge is introduced into the ring, apparently because of an electrostatic interaction.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 211–215, February, 1975.
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Romanova, K.I., Vinberg, L.B., Bogatkov, S.V. et al. Alkaline hydrolysis of benzoates and ϱ-nitrobenzoates of substituted 4-hydroxypiperidines. Chem Heterocycl Compd 11, 180–184 (1975). https://doi.org/10.1007/BF00471393
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DOI: https://doi.org/10.1007/BF00471393