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N-amination of 2,6-di-tert-butylpyridine

N-Aminierung von 2,6-di-tert-Butylpyridin

  • Anorganische Und Physikalische Chemie
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Summary

Despite its low nucleophilicity 2,6-di-tert-butylpyridine (DTBP) easily undergoes N-amination. Other hidered pyridines react similarly. Comparison of the NMR carbon chemical shifts of 2,6-disubstituted 1-aminopyridinium perchlorates and those of the respective 1-methylpyridinium salts shows that the changes are parallel. 1-Amino-2,6-di-tert-butylpyridinium perchlorate does not react withp-dimethylaminobenzaldehyde. However, other hindered 1-(4′-dimethylaminobenzylideneamino)pyridinium salts were obtained by a standard procedure.

Zusammenfassung

Trotz seiner geringen Nucleophilie ist an 2,6-Di-tert-butylpyridin (DTBP) leicht eine N-Aminierung durchzuführen. Andere gehinderte Pyridine reagieren ähnlich. Ein Vergleich der NMR-Kohlenstoffverschiebungen von 2,6-disubstituiertem 1-Aminopyridiniumperchlorat mit denjenigen der entsprechenden 1-Methylpyridiniumsalze zeigt, daß die Änderungen parallel verlaufen. 1-Amino-2,6-di-tert-butylpyridiniumperchlorat reagiert nicht mitp-Dimethylaminobenzaldehyd, hingegen wurden andere gehinderte 1-(4′-Dimethlylaminobenzylidenamino)pyridiniumsalze über Standardmethoden erhalten.

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Authors and Affiliations

  1. Institute of Chemistry, Pedagogical University, PL-25-020, Kielce, Poland

    Ryszard Gawinecki

  2. Robin Lane 5, 10994, West Nyack, NY, USA

    Bernard Kanner

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  1. Ryszard Gawinecki
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  2. Bernard Kanner
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Gawinecki, R., Kanner, B. N-amination of 2,6-di-tert-butylpyridine. Monatsh Chem 125, 35–41 (1994). https://doi.org/10.1007/BF00811671

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  • DOI: https://doi.org/10.1007/BF00811671

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