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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 19, Number 7
BKCSDE 19(7)
July 20, 1998 

Synthesis and Structure Identification of ABCH Type Calix[4]arenes : Two Step Synthesis of Asymmetrically Substituted Calix[4]arenes from Monoalkylcalix[4]arenes
Kye Chun Nam, Jong Min Kim, Young Ja Park
Several ABCH type chiral calix[4]arenes were prepared from monoalkyl calix[4]arenes by treating with various acyl halide, followed by reacting with benzoyl chloride in pyridine. These asymmetrically substituted ABCH type calix[4]arenes are obtained as racemates mixture which are confirmed by the chiral shift reagent in 1H NMR spectra. The molecular and crystal structure of 5-nitro-26-allyloxy-25-benzoyloxy-28-isobutyryloxy-27-hydroxycalix[4]arene 8a has been determined by the X-ray diffraction method. Two independent enantiomeric molecules are crystallized in a 1: 1 racemate mixture. They are in the partial cone conformation in which the benzoyloxy phenyl group is down. There is a bifurcated intramolecular hydrogen bonding involving three functional groups in each molecule.
770 - 776
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