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13C and 15N NMR spectra of 2,3-substituted 2H-azirines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The 13C and 15N NMR spectra of a series of 2,3-substituted 2H-azirines have been studied. The 15N chemical shift for the nitrogen in the azirine ring is found at much higher field than in acyclic imines with a considerable electronic effect for the substituents on the double bond. Cooperative steric and electronic effects associated with substituents on the unsaturated carbon atom of the ring were found to influence the shielding of the 13C and 15N nuclei. Reaction constants have been calculated for 2-alkyl(aryl)-3-phenylazirines. It has been shown that the azirine ring has a powerful —I effect (when compared with the phenyl ring) that exceeds the analogous value for the cyano group.

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Authors and Affiliations

  1. Institute of Organic Synthesis, Academy of Sciences of the Latvian SSR, 26006, Riga

    é. é. Liepin'sh, R. S. él'kinson, I. P. Piskunova & A. V. Eremeev

Authors
  1. é. é. Liepin'sh
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  2. R. S. él'kinson
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  3. I. P. Piskunova
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  4. A. V. Eremeev
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1181–1183, September, 1986.

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Liepin'sh, é.é., él'kinson, R.S., Piskunova, I.P. et al. 13C and 15N NMR spectra of 2,3-substituted 2H-azirines. Chem Heterocycl Compd 22, 953–955 (1986). https://doi.org/10.1007/BF00478123

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  • DOI: https://doi.org/10.1007/BF00478123

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