The Studies in the Synthesis of Chiral p-tert-butylcalix[4]arenes

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...

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Main Authors: Shi-yi Hsiao, 蕭世乙
Other Authors: Lee-gin Lin
Format: Others
Language:zh-TW
Published: 1999
Online Access:http://ndltd.ncl.edu.tw/handle/78875504301835666200
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spelling ndltd-TW-087PCCU05000302016-02-01T04:13:03Z http://ndltd.ncl.edu.tw/handle/78875504301835666200 The Studies in the Synthesis of Chiral p-tert-butylcalix[4]arenes 含有不對稱性之p-tert-Butylcalix[4]arenes的合成研究 Shi-yi Hsiao 蕭世乙 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. Lee-gin Lin 林立錦 1999 學位論文 ; thesis 88 zh-TW
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language zh-TW
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description 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.
author2 Lee-gin Lin
author_facet Lee-gin Lin
Shi-yi Hsiao
蕭世乙
author Shi-yi Hsiao
蕭世乙
spellingShingle Shi-yi Hsiao
蕭世乙
The Studies in the Synthesis of Chiral p-tert-butylcalix[4]arenes
author_sort Shi-yi Hsiao
title The Studies in the Synthesis of Chiral p-tert-butylcalix[4]arenes
title_short The Studies in the Synthesis of Chiral p-tert-butylcalix[4]arenes
title_full The Studies in the Synthesis of Chiral p-tert-butylcalix[4]arenes
title_fullStr The Studies in the Synthesis of Chiral p-tert-butylcalix[4]arenes
title_full_unstemmed The Studies in the Synthesis of Chiral p-tert-butylcalix[4]arenes
title_sort studies in the synthesis of chiral p-tert-butylcalix[4]arenes
publishDate 1999
url http://ndltd.ncl.edu.tw/handle/78875504301835666200
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