1-苯甲基-3-苯甲醯基calix[4]arene之苯甲醯基轉位的研究

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Title:	1-苯甲基-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-benzoyloxy-3-benzoyloxycalix[4]arenes system
Authors:	吳杰泰
Contributors:	化學系應用化學碩士班
Keywords:	苯甲基轉位 benzoyl-migration behavior
Date:	2013-07
Issue Date:	2013-09-13 13:26:51 (UTC+8)
Abstract:	Calixarenes是酚和甲醛在鹼性環境下，進行聚合反應所產生之環狀聚合物。而本論文主要的目的是在探討calix[4]arene系統中，苯甲醯基轉移之現象。在鹼環境中，p-tert-butylphenol和甲醛會進行聚合反應而形成黃綠色之聚合前驅物，將此聚合前驅物在二苯醚 (diphenyl ether) 進行迴流反應，可以轉換成p-tert-butylcalix[4]arene；利用三氯化鋁 (AlCl3)可進行反向的Friedel-Crafts 反應移除環狀聚合物上的對位三級丁基，而得到對位無取代之calix[4]arene。本實驗室在過去的研究中發現，calix[4]arene、甲醇鈉 (Sodium methoxide) 和過量的鹵化烷類在乙腈(Acetonitrile) 中迴流，可一步合成出單烷基醚化之 calix[4]arenes；所以本論文採用了碘化乙烷、溴化甲苯，來製備出單乙基醚化和單苯甲基醚化的calix[4]arenes。這些單烷基醚化之calix[4]arenes可分別再與benzoyl chloride、p-anisoylcloride進行酯化反應，而得到相對應的1-單烷基醚化-3-單苯甲酸酯化之化合物。如將這些1-單烷基醚化-3-單苯甲酸酯化在K2CO3的鹼性條件下，探討下緣的苯甲酸酯基之轉移反應的動力學研究，並以1H-NMR來對反應後的產物進行光譜解析，以推定其苯甲酸酯基轉換的程度。 The Calixarenes is progressed to react cyclic polymers of the polymerization by phenol and formaldehyde under the alkaline environment. In addition, the major aim of this paper is to explore a series of benzoyl in various p-alkoxy that substitutes the transfer phenomenon of the calix [4] arenes system. In the alkaline environment, p-tert-butylphenol and formaldehyde polymerization (polymerized) formed by the reaction of the chartreuse polymeric precursor, which combines with ether (diphenyl ether) to proceed the reflux reactions. It can be converting to p-tert-butylcalix [4] arene ; thus, utilizing the AlCl3 as a catalyst to progress reverse reaction of the Friedel-Crafts for removing the polymer on the bit cyclic tert-butyl (p-tert-butyl) in order to obtain the median substituted calix [4] arene. According to the previous laboratory research, calix [4] arene, excess halogenated alkanes (alkyl halides) and NaOCH3 refluxed in CH3CN, which can synthetize the mono-alkyl ether of calix [4] arenes in one step; Therefore, this paper utilizes the five halogenated of the alkanes ethane iodide (iodoethane), iodide propane (1-iodopropane), iodide butane (1-iodobutane), brominated toluene (benzyl-bromide), and allyl bromide (allyl bromide) to arrange this series of monoalkyl ether (monoalkylated) of calix [4] arenes. These calix [4] arenes of the monoalkyl ether can be further resulting the esterification reaction with benzoyl chloride, and acquiring 1 - monoalkyl ether -3 - esterifying a compound of a single acid. In conclusion, using 1 - monoalkyl ether of -3 - Single esterified acid under alkaline conditions in K2CO3 to research the lower edge of the benzoate ester transfer reaction kinetics, and applying 1H-NMR to the reaction product after the spectral resolution to be presumed benzoate base conversion level.
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