Exploiting the <i>p</i>‑Bromodienone Route for the Formation and Trapping of Calixarene Oxenium Cations with Enamine Nucleophiles

Published on 2018-05-16T12:42:56Z (GMT) by
This study shows that calixarene <i>p</i>-bromodienone derivatives can act as precursors for the formation of oxenium cations, which can be trapped with enamine <i>C</i>-nucleophiles. When calixarene <i>p</i>-bromodienones were treated with enamines, in the presence of AgClO<sub>4</sub>, the lower rim-substituted C–O–C products were obtained by an electrophilic attack of the intermediate calixarene-oxenium cation with a contemporary cone-to-partial-cone inversion of the involved aromatic ring.

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Soriente, Annunziata; Rosa, Margherita De; La Manna, Pellegrino; Talotta, Carmen; Gaeta, Carmine; Spinella, Aldo; et al. (2018): Exploiting the p‑Bromodienone Route for the Formation and Trapping of Calixarene Oxenium Cations with Enamine Nucleophiles. ACS Publications. Collection.