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Experimental and theoretical study of the reaction between bicyclo[2.2.1]hept-5-en-endo-2-ylmethylamine and 2-[(2-allylphenoxy)methyl]oxirane

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Abstract

In reactions of bicyclo[2.2.1]hept-5-en-endo-2-ylmethylamine with 2-[(2-allylphenoxy)methyl]oxirane alongside the product of amine monoalkylation a compound was obtained and isolated by chromatography on silica gel resulting from the reaction of the monoalkylated substance with the initial epoxide. The structure of new aminoalcohols and the regiochemistry of the oxirane opening were examined using IR, 1H NMR, and mass spectra. The features of the reaction mechanism were considered applying quantum-chemical calculations in the level of theory PCM/B3LYP/6-3aG(d).

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Authors and Affiliations

  1. Oles’ Honchar Dnepropetrovsk National University, Dnepropetrovsk, 49010, Ukraine

    V. A. Pal’chikov & L. I. Kas’yan

  2. Vinnichenko Kirovograd State Pedagogical University, Kirovograd, Ukraine

    L. K. Svyatenko

  3. Dnepropetrovsk Oblast State Center Protecting Soil fertility and Production Quality “Oblgosplodorodie”, Dnepropetrovsk, Ukraine

    I. N. Plakhotnii

Authors
  1. V. A. Pal’chikov
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  2. L. K. Svyatenko
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  3. I. N. Plakhotnii
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  4. L. I. Kas’yan
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Correspondence to V. A. Pal’chikov.

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Original English Text © V.A. Pal’chikov, L.K. Svyatenko, I.N. Plakhotnii, L.I. Kas’yan, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 5, pp. 704–708.

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Pal’chikov, V.A., Svyatenko, L.K., Plakhotnii, I.N. et al. Experimental and theoretical study of the reaction between bicyclo[2.2.1]hept-5-en-endo-2-ylmethylamine and 2-[(2-allylphenoxy)methyl]oxirane. Russ J Org Chem 49, 686–690 (2013). https://doi.org/10.1134/S1070428013050084

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  • DOI: https://doi.org/10.1134/S1070428013050084

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