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Research on 1-azabicyclic systems

XIII. Chemical methods for the separation of a mixture of epimeric 3-methylpyrrolizidines. relatively high basicities of the isomers

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Epimeric 3-methylpyrrolizidines were separated preparatively. Competitive quaternization of the mixture of isomers with n-propyl iodide and catalytic isomerization were used to obtain trans-3, 8-H-3-methylpyrrolizidine. cis-3,8-H-3-Methylpyrrolizidine was isolated from the mixture by quaternization with benzyl chloride and subsequent hydrogenolysis of the resulting quaternary salt. The pKa values of trans- and cis-3,8-H-3-methylpyrrolizidines, pyrrolizidine, and indolizidine were measured. It is shown that in a series of saturated amines with a tertiary nitrogen atom pyrrolizidine and 3-methylpyrrolizidines are among the strongest bases.

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Authors and Affiliations

  1. N. G. Chernyshevskii Saratov State University, USSR

    I. M. Skvortsov & I. V. Antipova

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  1. I. M. Skvortsov
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  2. I. V. Antipova
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See [1] for communication XII.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1060–1064, August, 1976.

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Skvortsov, I.M., Antipova, I.V. Research on 1-azabicyclic systems. Chem Heterocycl Compd 12, 876–879 (1976). https://doi.org/10.1007/BF00510106

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  • DOI: https://doi.org/10.1007/BF00510106

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