Exploiting the p‑Bromodienone Route for the Formation and Trapping of Calixarene Oxenium Cations with Enamine Nucleophiles
Version 2 2018-05-16, 12:42
Version 1 2018-05-16, 12:36
Posted on 2018-05-16 - 12:42
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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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. https://doi.org/10.1021/acs.joc.8b00431
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AUTHORS (7)
AS
Annunziata Soriente
MR
Margherita De Rosa
PL
Pellegrino La Manna
CT
Carmen Talotta
CG
Carmine Gaeta
AS
Aldo Spinella
PN
Placido Neri