Synthesis and Characterization of New Calixarenes from Bisphenol A

The synthesis of bisphenol A-derived calixarenes has been studied by changing the protecting group of the phe-nol moiety and reaction conditions. Depending on the protecting groups,the corresponding calix[6,7,8]arenes are obtained in different rat ios. For example, whcn mono-p-tert-butyldimethylsily...

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Published inBulletin of the Korean Chemical Society Vol. 21; no. 8; pp. 813 - 816
Main Authors 안교한, 김성곤, 유종선, An, Gyo Han, Kim, Seong Gon, Yu, Jong Seon
Format Journal Article
LanguageKorean
Published 2000
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Summary:The synthesis of bisphenol A-derived calixarenes has been studied by changing the protecting group of the phe-nol moiety and reaction conditions. Depending on the protecting groups,the corresponding calix[6,7,8]arenes are obtained in different rat ios. For example, whcn mono-p-tert-butyldimethylsilyl-protected bisphenol A is treated with paraformaldehyde and a catalytic amount ofaqueous KOH in refluxing p-xylene with a Dean-Stark water collector for 36 h, the corresponding calix[8]arene, calix[7]arene, and calix[6]arene are producedand separated in the ratio of about 3 : 2 : l and with overall 63% yield. The calixarenes are characterized by NMR spectroscopy and mass analysis. The X-raycrystal structure of the calix[8]arene shows a pleated loop confor-mation, stabilized by intramoIecular hydrogen bonding between the inner phenolic hydroxy groups.
Bibliography:KISTI1.1003/JNL.JAKO200013464477256
ISSN:0253-2964
1229-5949