Réactivité du nucléophile azoture vis à vis de cations hétérocycliques aromatiques. VI. Cas des triaryl-2,4,6 oxaziniums-1,3

• Published in: Canadian journal of chemistry Vol. 63; no. 1; pp. 86 - 94
• Main Authors: Cherton, Jean-Claude, Desbene, Paul-Louis, Bazinet, Marc, Lanson, Marc, Convert, Odile, Basselier, Jean-Jacques
• Format: Journal Article
• Language: English; French
• Published: Ottawa, Canada NRC Research Press 01.01.1985; National Research Council of Canada
• Subjects: Chimie; Chimie organique; Cinétique et mécanisme des réactions; Réactivité et mécanismes; Sciences exactes et technologie; Réaction nucléophile; Tétrazole(aryl-5 [diaryl-1p,3p oxo-3p propényl]-1); Cycle 6 chaînons; Régiosélectivité; Spectre RMN; Tautomérie cycle chaîne; Cycle 5 chaînons; Hétérocycle azote; Hétérocycle oxygène azote; Oxazine-1,3ium-1(triaryl-2,4,6); Anion minéral; Cation organique; Azoture
• ISSN: 0008-4042; 1480-3291
• DOI: 10.1139/v85-015

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/N 3 − system is discussed, together with results obtained from the 2,4,6-triphenylpyrilium/N 3 − .