Abstract
13C NMR spectra were obtained for pyrrolizidinium salts and their homologs and their signals were assigned. With the exception of highly strained cis-3,8-H-cis-5,8-H-3,5-dimethylpyrrolizidine (VI), all the bases studied upon their direct mixing with CF3CO2H form salts only with cis-fused rings in the cation. Mixtures of salts with cis- and trans-fused pyrrolizidinium fragments are formed upon the reaction of cis-3,8-H-methy1- (III) and cis-3,8-H-cis-5,8-H-3,5-dimethylpyrrolizidine (VI) under conditions close to those for kinetically-controlled amine protonation. The13C NHR spectra of the isomeric pyrrolizidinium salts obtained as a result of the absorption of base VI by sulfuric acid were used to evaluate the conformational equilibrium in the starting compound VI. The13C NMR chemical shifts of unsubstituted trans-fused pyrrolizidinium salts were predicted.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1638–1647, December, 1985
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Subbotin, O.A., Skvortsov, I.M. 1-azabicyclic compounds. 22. Stereochemistry and13C NMR spectra of salts of pyrrolizidine and its homologs with protonic acids. Chem Heterocycl Compd 21, 1347–1355 (1985). https://doi.org/10.1007/BF00842958
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DOI: https://doi.org/10.1007/BF00842958