The silver-mediated nucleophilic substitution on calixarene p-bromodienone derivatives (the 'p-bromodienone route') with activated aromatic substrates allows the introduction of aromatic moieties at the para- or meta-position of calixarene aromatic rings. Less reactive substrates mainly afford C-O para-coupled derivatives, while more activated ones mainly give inherently chiral, C-C meta-coupled products through a dienone-phenol rearrangement of the intermediate dienone derivative. Examples of C-C para-coupling and C-C coupling at the endo calixarene oxygen atom were also observed.

Appending aromatic moieties at the para- and meta-position of calixarene rings via p-bromodienone route

TROISI, FRANCESCO;GAETA, CARMINE;NERI, Placido
2009

Abstract

The silver-mediated nucleophilic substitution on calixarene p-bromodienone derivatives (the 'p-bromodienone route') with activated aromatic substrates allows the introduction of aromatic moieties at the para- or meta-position of calixarene aromatic rings. Less reactive substrates mainly afford C-O para-coupled derivatives, while more activated ones mainly give inherently chiral, C-C meta-coupled products through a dienone-phenol rearrangement of the intermediate dienone derivative. Examples of C-C para-coupling and C-C coupling at the endo calixarene oxygen atom were also observed.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11386/2281630
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