Synfacts 2009(4): 0387-0387  
DOI: 10.1055/s-0028-1087842
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

exo-Functionalization of Calixarene via a p-Bromodienone

Contributor(s): Timothy M. Swager, Ryan M. Moslin
F. Troisi, T. Pierro, C. Gaeta, P. Neri*
Università di Salerno, Fisciano (Salerno), Italy
Further Information

Publication History

Publication Date:
23 March 2009 (online)


Initiating from their previously described intermediate 2 (Tetrahedron Lett. 2003, 44, 9155), the authors present a mild and selective means to add alcohols to the exo rim of calixarenes. Reaction of 2 with silver perchlorate generates cation 3, which in turn reacts with the alcoholic nucleophile to give intermediate 4. Re­aromatization via loss of the tert-butyl cation then provides product 5. The strategy appears to have a very wide scope, as a broad range of alcohols are presented as viable substrates including, remarkably, acetic acid.