Stereospecificity of the addition of hydrogen cyanide to the carbonyl group of substituted 4-piperidones. Synthesis and three-dimensional structures of substituted 4-hydroxy-4-cyanopiperidines

Autor: Unkovskii, B. V., D'yakov, M. Yu., Sokolova, T. D., Rozhnov, V. B.
Zdroj: Chemistry of Heterocyclic Compounds; October 1990, Vol. 26 Issue: 10 p1132-1136, 5p
Abstrakt: Mixtures of stereoisomers of the corresponding 4-hydroxy-4-cyanopiperidines were synthesized by the reaction of substituted 4-piperidones with hydrogen cyanide by an exchange reaction with acetone cyanohydrin. The ratios of the stereoisomers in the resulting mixtures of stereoisomeric 4-piperidone cyanohydrins were determined by means of the 13C NMR spectra, and the three-dimensional structures were established by direct determination of the orientation of the cyano group in their molecules. A dependence of the quantitative ratios of the stereoisomeric cyanohydrins of the substituted 4-piperidones on the reaction temperature was demonstrated.
Databáze: Supplemental Index
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