Oxygenation of calixarene phenol rings.
[structure: see text] The first examples of epoxy-p-quinol and diepoxy-p-quinol calixarene derivatives have been obtained by base-promoted direct addition of O(2)(oxygenation) to calixarene phenol rings. The regio- and stereochemistry of these derivatives was determined by 2D NMR studies, in conjunction with MM3 calculations, and X-ray crystallography. Both the oxygenation and the subsequent carbonyl reduction occur with a preferential attack to the less hindered exo face of the calixarene rings.
Dipartimento di Chimica, Università di Salerno, Via S. Allende 43, I-84081 Baronissi (Salerno), Italy.
Carmine
C
Gaeta
Francesco
F
Troisi
Marco
M
Martino
Enrico
E
Gavuzzo
Placido
P
Neri