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Synthesis and structures of new chiral diamide-ester macrocycles
✍ Scribed by Ming Zhang Gao; Joseph H. Reibenspies; Ralph A. Zingaro; Bo Wang; Zun Le Xu
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 2004
- Tongue
- English
- Weight
- 338 KB
- Volume
- 41
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
Abstract
A series of new hetero‐macrocyclic diamide‐ester compounds (4a — 4z, 6a — 6b) were synthesized using 4‐(dimethylamino)pyridine as catalyst and characterization by infrared spectra, nuclear magnetic resonance spectra, mass spectra and elemental analyses. The structures of 4e and meso 4b were determined by X‐ray crystallography. The association constants of the compounds with various metal ions were determined by UV‐visible spectroscopic titration, and showed a selective recognition for certain metal ions.
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## Abstract For Abstract see ChemInform Abstract in Full Text.
## Abstract A synthesis of a series of macrocyclic diamides **3** in good yields by reacting the corresponding bis phenols **4** with the appropriate dihalo alkanes **6** either in solvent or in dry media under microwave irradiation. Thiation of **3** with P~2~S~5~ or Lawesson's reagent in solvent
tetrathiacyclooctadecane (3) have been obtained by intermolecular cyclization of 1,3-bis(2-bromoethyl)adamantane (4) with thioacetamide using a high-dilution technique. The reaction is concentration-dependent. The crystal structures of 1, 2, and 3 have been determined by single-crystal X-ray diffra