This study shows that calixarene p-bromodienone derivatives can act as precursors for the formation of oxenium cations, which can be trapped with enamine C-nucleophiles. When calixarene p-bromodienones were treated with enamines, in the presence of AgClO4, 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.

Exploiting the p-Bromodienone Route for the Formation and Trapping of Calixarene Oxenium Cations with Enamine Nucleophiles

SORIENTE, Annunziata
Conceptualization
;
De Rosa Margherita
Membro del Collaboration Group
;
LA MANNA, PELLEGRINO
Membro del Collaboration Group
;
TALOTTA, Carmen
Membro del Collaboration Group
;
Gaeta Carmine
Conceptualization
;
SPINELLA, Aldo
Membro del Collaboration Group
;
NERI, Placido
Supervision
2018-01-01

Abstract

This study shows that calixarene p-bromodienone derivatives can act as precursors for the formation of oxenium cations, which can be trapped with enamine C-nucleophiles. When calixarene p-bromodienones were treated with enamines, in the presence of AgClO4, 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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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11386/4715116
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