| Summary: | 碩士 === 中國文化大學 === 應用化學研究所 === 87 === Calixarenes, which are cyclic oligomers of phenol and formaldehyde, are able to include small organic molecules or metal ions within the molecular cavities to form the "host-guest complexes". The main purpose of this thesis is to re-examine the possible application of the Chung and Lin's procedure, and subsequently, synthesizes the corresponding p-tert-butylcalix[4]arenes with four different substituents on their "lower rim".
p-tert-Butylphenol was condensed with aqueous formaldehyde under basic conditions to give an yellowish "precursor", which was then converted to p-tert-butyl-calix[4]arene by refluxing in diphenyl ether. By following the Chung and Lin's six-step synthetic procedure, the p-tert-butylcalix[4]arene was then transformed to the target products.
Due to the difference between calix[4]arene and p-tert-butylcalix[4]arene, the benzoylation of p-tert-butyl-calix[4]arene and it's derivatives was studied in this thesis in more detail. Treatment of p-tert-butyl-calix[4]arene with benzoyl chloride under various reaction conditions produced only the tribenzoate 26. Treatment of 1,3-dialkyl ether 25 with benzoyl chloride under different reaction conditions yielded both the monobenzoate 27 and dibenzoate 28 in variuos amount. All products that were prepared in this thesis were characterized by 1H-NMR and FAB-MS, and the synthetic procedure were also discussed.
|
|---|
