Synthesis and Host Properties of (1,3)- p-tert-Butylcalix[5]crown-6 Derivatives Incorporating the 1,1'-Binaphthalene-2,2'-dioxy Subunit |
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Authors: | Salvatore Caccamese Anna Notti Sebastiano Pappalardo Melchiorre F Parisi Grazia Principato |
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Institution: | (1) Dipartimento di Scienze Chimiche, Universitá di Catania, Viale A. Doria 6, I-95125 Catania, Italy;(2) Dipartimento di Chimica Organica e Biologica, Universitá di Messina, Salita Sperone 31, I-98166 Vill. S. Agata, Messina, Italy |
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Abstract: | Alkylation of p-tert-butylcalix5]arene (1) with 2,2'-bis(5-tosyloxy-3-oxa-1-pentyloxy)-1,1'-binaphthalene ((±)-2) in the presence of CsF affords selectively racemic 1,3-bridged calix5] 5]crown-6-triol 3, along with very small amounts of the (1,2)-bridged regioisomer 4. Compound 3 has been converted into tri-methoxy and tri--picolyloxy derivatives 5 and 6, respectively, by exhaustive alkylation with the appropriate electrophile and base. The direct separation of the enantiomers of racemates 3 and 6 was achieved by HPLC, using a chiral stationary phase (Chiralpak AD). Hosts 5 and 6 are able to selectively form 1 : 1 endo-cavity complexes with the linear RNH3
+ ions. |
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Keywords: | Chiral calixarene crown ethers separation of enantiomers molecular recognition RNH3
+ inclusion complexes |
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