MERZ, A and KARL, A and FUTTERER, T and STACHERDINGER, N and SCHNEIDER, O and LEX, J and LUBOCH, E and BIERNAT, JF (1994) SYNTHESES AND REACTIONS OF CROWN ETHER-BRIDGED STILBENES. LIEBIGS ANNALEN DER CHEMIE (12). pp. 1199-1209. ISSN 0170-2041,
Full text not available from this repository.Abstract
A high-yield synthesis of o,o' crown ether-bridged stilbenes 3b-e by reductive McMurry condensation of (2-formylphenyl)oligoethylene glycols 2b-e with facile (E/Z) diastereomer separation by selective cation complexation is described. Derivatization of the stilbene double bonds of (E)- or (Z)-3b-e affords dihydroxy crown ethers 4c, d and 5c, d diastereo- and enantioselectively. Likewise, trans- and cis-epoxides 11b-d and 12b-d are stereospecifically obtained. A crown ether-bridged diphenylacetaldehyde 13 is formed by rearrangement of Ile or 12c. Photocyclization of 3e yields large-ring 1,8-phenanthrene crown ether 18. The crystal structures of racemic 5c and of 12d are presented. A high caesium selectivity compared to the other alkali metal and alkaline earth cations is found for ion exchange membranes with incorporated crown ether (Z)-3c.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | CATALYZED ASYMMETRIC DIHYDROXYLATION; SUPRAMOLECULAR CHEMISTRY; MOLECULAR RECOGNITION; VICINAL HYDROXYLATION; OLEFINS; COMPLEXES; PERSPECTIVES; LECTURE; SYSTEMS; LEADS; MCMURRY REACTION; CROWN ETHERS; HYDROXYLATION, ENANTIOSELECTIVE; ION EXCHANGE MEMBRANES |
| Depositing User: | Dr. Gernot Deinzer |
| Last Modified: | 19 Oct 2022 08:39 |
| URI: | https://pred.uni-regensburg.de/id/eprint/52950 |
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