25,26-Dialkoxycalix[4]arenes. Part 1: 25-Alkoxy-26,27-diacetoxy route

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Title:	25,26-Dialkoxycalix[4]arenes. Part 1: 25-Alkoxy-26,27-diacetoxy route
Authors:	Wu, FY (Wu, Fung-Ying) Chang, KF (Chang, Kai-Fu) Kuo, CH (Kuo, Cheng-Han) Chen, KC (Chen, Kuan-Chih) Lee, KC (Lee, Kuo-Chang) Huang, CS (Huang, Chiun-Shiang) Chiang, YS (Chiang, Yung-Sheng) Lin, LG (Lin, Lee-Gin)
Contributors:	Inst Appl Chem
Keywords:	POSSIBLE CONFORMATIONAL ISOMERS LOWER RIM SELECTIVE FUNCTIONALIZATION CALIX<4>ARENES CALIXARENES ALKYLATION SUBSTITUENTS
Date:	2011-05-06
Issue Date:	2013-01-18 11:12:16 (UTC+8)
Abstract:	Acetylation of calix[4]arene 1,3-dialkyl ethers yielded the corresponding monoacetates. The (1)H NMR spectral analysis indicated that the products' alkoxy moieties were 'rotation restricted'. Acylation of calix [4]arene monoalkyl ethers with acetyl chloride yielded monoacetates and/or 2,3-diacetates in different reaction conditions. A simple recrystallization process was able to isolate 2,3-diacetates in good yield. The (1)H NMR spectra of the diacetylated products indicated that those compounds also possessed the 'rotation restricted' alkoxy moieties. In the presence of K(2)CO(3) as reaction base, alkylation of 2,3-diacetates produced the acetyl-migrated 1,3-dialkyloxy derivatives. Basic hydrolysis of the acetyl-migrated compounds yielded the known 1,3-dialkoxycalix[4]arenes. In the presence of NaH as reaction base, 2,3-diacetates were alkylated with and without the acetyl-migration. For the highly reactive benzyl bromide and allyl bromide, the majority of alkylation proceeded without acetyl-migration. In the other alkyl halides, the products were the acetyl-migrated 1,3-dialkoxy derivatives along with less than one-fourth the amount of non-migrated 1,2-dialkoxy derivatives. (C) 2011 Elsevier Ltd. All rights reserved.
Relation:	TETRAHEDRON Volume: 67 Issue: 18 Pages: 3238-3247
Appears in Collections:	[Department of Chemistry & Graduate Institute of Applied Chemistry ] journal articles

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