1-丁基-3-苯甲醯基calix[4]arene之苯甲醯基轉位的研究

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Title:	1-丁基-3-苯甲醯基calix[4]arene之苯甲醯基轉位的研究 The Study of The Benzoyl-migration Behavior in 1-Butoxy-3-benzoyloxycalix[4]arene System
Authors:	黃琮民
Contributors:	化學系應用化學碩士班
Date:	2014
Issue Date:	2014-10-06 10:35:14 (UTC+8)
Abstract:	在鹼性環境中，三級丁基酚和甲醛會進行聚合反應而形成黃綠色的聚合前驅物。此前驅物在二苯醚中迴流，可被轉換為p-tert-butylcalix[4]arene；如再利用三氯化鋁進行反向的Friedel-Crafts 反應，來移除環狀聚合物上的對位三級丁基，便可得到對位無取代之 calix[4]arene(6)。 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, via AlCl3-catalyzed reverse Friedel-Crafts reaction, to give the calix[4]arene(6). Calixarenes, which are cyclic oligomers, are able to include small organic molecules or metal ions within molecular cavities to form the “host-guest complexes”. This property can be used in the research area of ion separation,trace metals detection, and enzyme mimic. The main purpose of this thesis is to study the benzoyl-migration behavior in 1-ethoxy-3-benzoyloxycalix[4]arenes(30,35,40)and 1-butoxy-3-benzoyloxycalix[4]arenes(32,37,42) systems. In according to our previous studies in the present of sodium methoxide, calix[4]arene was able to yield the monoalkylatecalix[4]arenes (25-29),in one-step by refluxing with various alkyl halides in acetonitrile. The monoalkylatecalix[4]arenes were converted to various benzoated products (33-40) by esterified with different benzoyl chlorides in pyridine were converted to various benzoated.Under basic condition, 1-monoalkyloxy-3-benzoyloxycalix[4]arenes,were transformed via benzoyl-migration pathway to 1-alkoxy-2-benzoyloxy calix[4]arenes. The purpose of this thesis the kinetic phenomena of the benzoyl-migration,and the benzoyl-migration products.Migration product was isolated,purified,andidentified with 1H-NMR.
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