Réactivité du nucléophile azoture vis à vis de cations hétérocycliques aromatiques. VI. Cas des triaryl-2,4,6 oxaziniums-1,3
| Autor: | Marc Bazinet, Odile Convert, Jean-Claude Cherton, P.L. Desbene, Marc Lanson, Jean-Jacques Basselier |
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| Rok vydání: | 1985 |
| Předmět: |
chemistry.chemical_classification
Organic Chemistry chemistry.chemical_element Regioselectivity Oxazines General Chemistry Nuclear magnetic resonance spectroscopy Kinetic control Tautomer Medicinal chemistry Catalysis chemistry.chemical_compound chemistry Nucleophile Sodium azide Organic chemistry Carbon |
| Zdroj: | Canadian Journal of Chemistry. 63:86-94 |
| ISSN: | 1480-3291 0008-4042 |
| DOI: | 10.1139/v85-015 |
| Popis: | Nucleophilic attack of sodium azide on 2,4,6-triaryl-1,3-oxazinium species gives high yields of β-tetrazolo-trans-benzalacetophenones from the corresponding 2-azido-1,3-oxazines. The rearrangement of the azido oxazines likely proceeds via tautomerism of the intermediate iminoazides. If the formation of the 2-azido-1,3-oxazines is under kinetic control, these results are a rare example of high regioselectivity in nucleophilic attack at the C2 carbon of 1,3-oxazinium species.The reaction behaviour of the 1,3-oxazinium/N3− system is discussed, together with results obtained from the 2,4,6-triphenylpyrilium/N3−. |
| Databáze: | OpenAIRE |
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