A One-Pot Synthesis of New Macrocyclic Compounds with Tetraaminoethene Substructure
✍ Scribed by Matthias Wenzel; Rainer Beckert; Wolfgang Günther; Helmar Görls
- Publisher
- John Wiley and Sons
- Year
- 1998
- Tongue
- English
- Weight
- 444 KB
- Volume
- 1998
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
A convienent one-pot synthesis of macrocycles containing a bis(thiocarbamoyl) derivatives 3. In the final step, a ringclosure reaction using a large number of α,ω-dielectrophilic tetraaminoethene substructure is described. Starting from oxalic amidines 1, reduction with lithium and subsequent building blocks yields the new macrocyclic compounds 6-14. addition of phenyl isothiocyanate afforded the anionic Macrocyclic compounds present a very large variety of various donor atoms. These crowns readily coordinate with heavy metal ions, forming endocyclic Ag I [6] [7] and structures and properties ranging from the ligand to the complex and from the receptor to the supermolecule. A Hg II [8] complexes. The dithiomaleonitrile substructure bears an electron-deficient CϭC double bond and therefore large number of macrocyclic ligands with different ring sizes and various heteroatom sequences have been synthe-reduces the σ-donating ability of the sulfur atoms. Thus, the normally thiophilic metal ions preferentially coordi-sized [1] [2] [3] . The scientific and practical interest in such complexing species is undeniable. There are numerous ap-nate to the macrocyclic oxygen atoms. In contrast, macrocycles with an electron-rich CϭC double bond seem to be plications of macrocyclic complexing agents in the fields of ion transport, analytical chemistry, bioorganic model sys-of interest because of their interaction with metal cations and in connection with possible electron-transfer pro-tems, and phase-transfer catalysis.
Recently, Märkl et al. [4] and Hoffman et al. [5] have de-cesses. These circumstances encouraged us to synthesize macrocycles which contain an electron-rich CϭC double scribed a general synthetic method for the incorporation of the dithiomaleonitrile unit into macrocycles containing bond.
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obtained with the expensive Wilkinson catalyst ([