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Synthesis 2001; 2001(4): 0607-0611
DOI: 10.1055/s-2001-12344
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Synthesis of Calix[4]arene Derivatives with Alkyl Guanidinium or Chiral Bicyclic Guanidinium

Fang Liu* , Guo-Yuan Lu, Wei-Jiang He, Jun Hu, Yu-Hua Mei, Long-Gen Zhu
  • *Department of Chemistry, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, P. R. China; Fax + 86(25)3 31 77 61; E-mail: nnj.lugy@jlonline.com
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Publikationsdatum:
31. Dezember 2001 (online)

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A series of p-tetra-tert-butyl calix[4]arene derivatives with alkyl guanidinium or chiral bicyclic guanidinium functionalities were synthesized as the receptors of organic anions. Mono- and di-alkyl guanidinium derivatives were prepared by the reaction of 5,11,17,23-tetra-tert-butyl-25,27-(2-aminoethoxy)-26,28-dihydroxy calix[4]arene (1) with methyl isothiourea sulphate. While mono- and di-chiral bicyclic guanidinium derivatives were all obtained via an O-alkylation reaction of p-tetra-tert-butyl calix[4]arene with chloromethyl chiral bicyclic guanidinium (6 or 7) in the presence of anhydrous K2CO3 in acetonitrile, good yields were only observed for mono-substituted derivatives.

functionalized calix[4]arene - synthesis - alkyl guanidinium - chiral bicyclic guanidinium - molecular recognition