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Research on 1-aza two-ring systems

XVII. Synthesis of 5-(γ-hydroxypropyl)-1,2-dihydropyrrolizines and properties of their intramolecular π-hydrogen bonds

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Reduction of 5-[2-(methoxycarbonyl)ethyl]-1,3-dihydropyrrolizines with lithium aluminum hydride gave 5-(γ-hydroxypropyl)-1,2-dihydropyrrolizines (in 70–90% yields), which have intramolecular π-hydrogen bonds in dilute solutions. The parameters of the π-hydrogen bonds were determined in the IR spectra, and their enthalpies were found. The data obtained (ΔνOH 95–99 cm−1, −ΔH 3.05 kJ·mole−1) show that among compounds with an aliphatic hydroxyl group and a system of π electrons, 5-(γ-hydroxypropyl)-1,2-dihydropyrrolizines have some of the strongest intramolecular π-hydrogen bonds.

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Authors and Affiliations

  1. N. G. Chernyshevskii Saratov State University, 410601, Saratov

    I. M. Skvortsov, L. N. Astakhova, S. N. Kuz'min & I. Ya. Evtushenko

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  1. I. M. Skvortsov
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  2. L. N. Astakhova
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  3. S. N. Kuz'min
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  4. I. Ya. Evtushenko
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Additional information

See [1] for communication XVI.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 359–363, March, 1978.

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Skvortsov, I.M., Astakhova, L.N., Kuz'min, S.N. et al. Research on 1-aza two-ring systems. Chem Heterocycl Compd 14, 293–297 (1978). https://doi.org/10.1007/BF00470562

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  • DOI: https://doi.org/10.1007/BF00470562

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