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    Please use this identifier to cite or link to this item: https://irlib.pccu.edu.tw/handle/987654321/24037


    Title: 25,26-Dialkoxycalix[4]arenes. Part 2: 1-Alkoxy-3-benzoyloxy route
    Authors: Kuo, CH (Kuo, Cheng-Han)
    Huang, JR (Huang, Jun-Ren)
    Chen, HR (Chen, Hui-Ru)
    Chen, PY (Chen, Pei-Yu)
    Lin, CH (Lin, Chien-Hung)
    Lin, LG (Lin, Lee-Gin)
    Contributors: Inst Appl Chem
    Keywords: LOWER RIM
    SELECTIVE FUNCTIONALIZATION
    CALIX<4>ARENES
    ALKYLATION
    ISOMERS
    CONFORMATION
    SUBSTITUENTS
    CALIXARENES
    Date: 2011-05-27
    Issue Date: 2013-01-18 10:37:36 (UTC+8)
    Abstract: Benzoylation of calix[4]arene monoalkyl ethers with benzoyl chloride yielded the corresponding 3-benzoates and/or 2,3-dibenzoates in different reaction conditions. A simple recrystallization process was able to isolate the 3-benzoates in good yield. In the presence of NaH as reaction base, the 1-alkoxy-3-benzoyloxycalixarenes were alkylated with active alkyl halides at proximal position and yielded the corresponding 1,2-dialkoxy derivatives. Basic hydrolysis of compounds afforded the expected 25,26-dialkoxycalix[4]arenes. For the less active alkyl halides, alkylation of 1-alkoxy-3-benzoyloxycalix[4]arenes afforded both the 1,2-dialkoxy derivatives and the benzoyl-migrated 1,3-dialkoxy derivatives. Only the highly symmetrical 1,3-diethoxy-2-benzoyloxycalix[4]arene was able to be isolated upon the deliberate recrystallization process. After basic hydrolysis of the dialkylated crude products, 25,26-dialkoxycalix[4]arenes were chromatographic separated. (C) 2011 Elsevier Ltd. All rights reserved.
    Relation: TETRAHEDRON Volume: 67 Issue: 21 Pages: 3936-3944
    Appears in Collections:[Department of Chemistry & Graduate Institute of Applied Chemistry ] journal articles

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