Calixarenes, which are cyclic oligomers of p-substituted phenols and formaldehyde, are able to include small organic molecules or metal ions within molecular cavities to form the “host-guest complexes”. This phenomenon has been proposed in the research area of micro-analysis detection devices, ion separation, and enzyme-mimic studies. The main purpose of this thesis is to study the benzoyl-migration behavior in 1-ethoxy-3-benzoyloxycalix[4]arenes systems.
In the present of a base, p-tert-butylphenol and formaldehyde were polymerized to form a yellowish precursor. By refluxing of this precursor in diphenyl ether yielded the p-tert-butylcalix[4]arene. The p-tert-butyl groups were then removed by AlCl3-catalyzed that will follow a reverse Friedel-Crafts reaction to give a para calix[4]arene(6).
In our earlier studies on the series of calix[4]arene, we have noticed that in the present of sodium methoxide as the reacting base. The monoalkylated calix[4]arenes can be prepared by refluxing of calix[4]arene with different kind of alkyl halides in acetonitrile yielded monoalkylate claix[4]arenes as the main products (25-29).
Esterification of those monoalkylated calix[4]arenes (25-29) with an excess of benzoyl chloride in pyridine produced the corresponding 1-alkoxy-3-benzoyloxycalix[4]arenes (30-34)、(35-39)、(40-44) . There- fore, the final purpose of this studies is those products under basic condit- ion to study its kinetic transformation of benzoyl and then after separation, by using 1H-NMR,13C-NMR and COSY to identify those products.
